J. Org. Chem., 1996, 61(11), 3849-3862, DOI:10.

1021/jo960057x

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(01996 American Chemical Society Journal Of Organic Chemistry V61 Page 3849 Abdel-Magid Supplemental Page 1

N,1-Dicyclobutvlbenzylamine: (Table I, entry 1)

Ph- CH 2 -N

HCI salt: a white solid, mp 183-184 'C (EtOAc/MeOH). FT-IR (KBr) 2973 (s), 2949 (s), 2881 (m)
2825 (s), 1600 (s), 1505 (s), 1285 (s), 1235 (vs), 1145 (s), 1100 (vs), 926 (s), 750 (s) cm- 1 ; 1H NMR
(CDCl3) 8 12.7 (bs, 1H), 7.47-7.40 (m, 5H), 4.08 (s, 2H), 3.40-3.30 (m, 2H), 3.02-2.85 (m, 4H),
2.30-2.00 (m, 4H), 1.98-1.88 (m, 2H), 1.76-1.60 (m, 2H); 13C NMR (CDCl3) 8 131.1 (CH), 129.9
(CH), 129.1 (CH), 127.5 (C), 56.6 (CH), 51.6 (CH2), 27.4 (CH2), 27.2 (CH2), 15.1 (CH2); El MS

n/z (relative intensity) 215 (M+, 5), 187 (13), 186 (8), 159 (29), 158 (20), 131 (14), 96 (15), 91 (100).
Analysis calculated for C15H22CIN: C, 71.55; H, 8.81; N, 5.56; Cl, 14.08. Found: C, 71.22; H, 8.77;
N, 5.59; Cl, 14.12.

1-Cyclobutvl-4-phenylpiperazine: (Table I, entry 3)

Ph-N N

Oxalate salt: a tan white solid, mp 225-227 OC (EtOAc/MeOH). FT-IR (KBr) 3061 (m), 2997 (s), 2955
(s), 2849 (s), 2589 (s), 2453 (s), 1950 (m), 1719, (s), 1595 (s), 1500 (s), 1446 (s), 1399 (s), 1235 (s),
1189 (s), 1101 (s), 1020 (s), 920 (s), 762 (s), 721 (s), 420 (m) cm- 1; 1H NMR (free amine, CDCl3) 8

7.26 (dd, J = 7.9, 7.2 Hz, 2H), 6.93 (d, J = 7.9 Hz, 2H) 6.85 (t, J = 7.2 Hz, 1H), 3.21 (t, J = 5.1 Hz,
4H), 2.84-2.73 (m, 1H), 2.49 (t, J = 5.1 Hz, 4 H), 2.10-1.99 (m, 2H), 1.98-1.86 (m, 2H), 1.79-1.69
(m, 2H); 13 C NMR (free amine, CDCl3) 8 151.4 (C), 129.1 (CH), 119.7 (CH), 116.1 (CH), 60.3
(CH), 49.5 (CH2), 48.9 (CH2), 27.0 (CH2), 14.3 (CH2); El MS m/z (relative intensity) 216 (M+, 16),

188 (56), 173 (9), 146 (14), 132 (100), 119 (41), 105 (29), 104 (28), 91 (9), 77 (26), 55 (30).

Analysis calculated for C16 H2 2 N2 0 4 : C, 62.73; H, 7.24; N, 9.14. Found: C, 62.60; H, 7.23; N, 8.99.
(01996 American Chemical Society Journal Of Organic Chemistry V61 Page 3849 Abdel-Magid Supplemental Page 2

N-(1-Propyl) aminocycloheptane: (Table I, entries 6 & 7)

HCl salt: a white solid, mp 207-208 oC (EtOAc/MeOH). FT-IR (KBr) 3262(m), 2939(s), 2811(s),
2515(w), 1460(m) cm- 1; 1H NMR (CDCl 3 ) 8 9.46 (bs, 2H), 3.17-3.10 (m, 1H), 2.92-2.84 (m, 2H),

2.27-2.21 (m, 2H), 2.05-1.92 (m, 2H), 1.90-1.80 (m, 4H), 1.60-1.55 (m, 4H), 1.52-1.42 (m, 2H),
0.99 (t, J = 7.3 Hz, 3H); 13 C NMR (CDCl 3 ) 8 59.2 (CH), 46.3 (CH 2 ), 30.7 (CH 2 ), 27.5 (CH 2 ), 23.9
(CH 2 ), 19.5 (CH2 ), 11.3 (CH 3 ); CI MS m/z (relative intensity) 156 (MH+, 26), 155 (39), 154 (80), 126
(41), 112 (15), 98 (100), 97 (19), 83 (13), 83 (23), 70 (12), 60 (50). Analysis calculated for
C10 H22 CIN: C, 62.64; H, 11.56; N, 7.30; Cl, 18.49. Found: C, 62.60; H, 11.75; N, 7.26; Cl, 18.47.

N-Cyclooctyl-m-methoxvbenzvlamine: (Table I, entry 8)

CH2-Q
OCH3

HC1 salt: a white solid, mp 199-200 oC (EtOAc/MeOH). FT-IR (KBr) 3400(w), 2974 (s), 2925 (s),
2850 (s), 2799 (s), 2673 (s), 2462 (m), 1602 (s), 1577 (s), 1469 (s), 1437 (s), 1307 (m), 1266 (s),
1179 (s), 1034 (s), 791 (s), 695 (s) cm- 1 ; 1 H NMR (CDCl 3 /DMSO-d 6 ) 8 9.45 (bs, 2H), 7.35 (s, 1H),

7.29 (t, J = 7.9 Hz, 1H), 7.15 (d, J = 7.9 Hz, 1H), 6.91 (d, J = 7.9 Hz, 1H), 4.10-4.05 (m, 2H), 3.83
(s, 3H), 3.25-3.10 (m, 1H), 2.20-2.00 (m, 2H), 1.90-1.70 (m, 4H), 1.70-1.40 (m, 6H); 13 C NMR
(CDCl 3 / DMSO d6 ) 8 161.1 (C), 134.4 (C), 131.1 (CH), 123.6 (CH), 116.9 (CH), 116.2 (CH), 58.9
(CH2), 56.8 (CH3), 49.2 (CH), 30.4 (CH2), 27.5 (CH2), 27.0 (CH2), 25.1 (CH2); EI-MS m/z

(relative intensity) 247 (M+, 4), 204 (9), 190 (5), 176 (56), 162 (7), 145 (19), 137 (7), 136 (12), 126
(23), 122 (15), 121 (100), 106 (6), 91 (26), 78 (15), 77 (14). Analysis calculated for Cl6H26 ClNO: C,
67.71; H, 9.23; N, 4.93; Cl, 12.49. Found: C, 67.72; H, 9.22; N, 4.80; Cl, 12.56.
(01996 American Chemical Society Journal Of Organic Chemistry V61 Page 3849 Abdel-Magid Supplemental Page 3

N-Cyclododecyl-2-aminoacetaldehyde dimethylacetal: (Table 1, entry 9)

OEt

OEt

Oxalate salt: a white solid, mp 173-174 oC (MeOH). FT-IR (KBr) 3429 (w), 2931 (s), 2860 (s), 2774

(w), 1720 (m), 1634 (m), 1566 (m), 1467 (m), 1407 (m), 1145 (s), 1075 (s), 721 (s), 500 (m) cm- 1; 1H
NMR (free base, CDCl 3 ) 8 4.59 (t, J = 5.6 Hz, 1H), 3.70 (dq, J = 45.2, 7.2 Hz, 2H), 3.55 (dq, J =

45.2, 7.2 Hz, 2H), 2.72 (d, J = 5.6 Hz, 2H), 2.62 (m, 1H), 1.55-1.33 (m, 23 H), 1.22 (t, J = 7.2 Hz,
6H); 13C NMR (free base, CDCl 3 ) 8 102.3 (CH), 62.1 (CH 2 ), 54.5 (CH), 49.7 (CH 2 ), 29.1 (CH )
2

24.8 (CH 2 ), 24.3 (CH2), 22.9 (CH 2 ), 22.8 (CH 2 ), 20.6 (CH 2 ), 15.2 (CH 3 ); EI-MS m/z (relative
intensity) 299 (M+., 1), 254 (17), 196 (90), 103 (100), 47 (57). Analysis calculated for C20 H 39 N0 6 : C,
61.67; H, 10.09; N, 3.60. Found: C, 61.79; H, 10.16; N, 3.43.

2-(Morpholin-4-yl)-1.2.3.4-tetrahydronaphthalene: (Table I, entry 11)

NO

HCI salt: a white solid, mp 262-263 OC (EtOAc/MeOH). FT-IR (KBr) 3392(s), 2939(m), 2674(s),

2617(s), 2538(m), 2471(m), 1460(m), 1398(m), 1256(m), 1118(s), 976(m), 872(s), 756(s) cm- 1; 1H
NMR (DMSO-d6/D 2 0) 8 7.30-7.04 (m, 4H), 4.25 (d, J = 4.0 Hz, 2H), 3.95 (t, J = 4.0 Hz, 2H), 3.69

(t, J = 3.0 Hz, 3H), 3.38 (m, 3H), 3.03 (m, 2H), 2.95 (m, 1H), 2.50 (m, 1H), 1.90 (m, 1H); 13 C

NMR (DMSO-d 6 /D 2 0) 8 132.4(C), 129.6 (C), 126.9 (CH), 126.2 (CH), 124.5 (CH), 124.1 (CH),

61.3 (CH 2 ), 60.3 (CH), 46.4 (CH 2 ), 64.1 (CH 2 ), 26.8 (CH 2 ), 25.0 (CH 2 ), 20.9 (CH 2 ); El MS m/z
(relative intensity) 217 (M+, 86), 216 (10), 159 (10), 158 (18), 144 (25), 131 (37), 130 (100), 129
(51), 128 (35), 127 (16), 126 (14), 117 (15), 116 (21), 115 (46), 113 (14), 112 (72), 104 (21), 103

(16), 100 (10), 98 (16), 91 (39), 86 (19), 78 (17), 77 (20), 68 (12), 55 (29). Analysis calculated for
C 16 H24 CIN: C, 66.26; H, 7.94; N, 5.52; Cl, 13.97. Found: C, 66.37; H, 8.12; N, 5.47; Cl, 14.18.
(01996 American Chemical Society Journal Of Organic Chemistry V61 Page 3849 Abdel-Magid Supplemental Page 4

47

N-Phenyl-1,2.3.4-tetrahydro-2-aminonaphthalene: 30 (Table I, entry 12)

CIN-Ph

HCI salt, a white solid that turns tan on standing, mp 197-199 oC (EtOAc/MeOH) (lit. 31 193-196 0 C).
FT-IR (KBr) 3433 (m), 2929 (m), 2726 (s), 2682 (s), 2624 (s), 2471 (s), 1589 (w), 1492 (s), 1449
(m), 755 (s), 691 (m) cm- 1; 1H NMR (DMSO-d 6 ) 8 11.4 (bs, 1H), 7.71 (d, J = 7.8 Hz, 2H), 7.54 (dd,

J = 7.8, 7.3 Hz, 2H), 7.45 (t, J = 7.3 Hz, 1H), 7.10-6.90 (m, 4H), 3.95-3.80 (m, 1H), 3.20-3.00 (m,
2H), 2.90 - 2.70 (m, 2H), 2.30-2.20 (m, 1H), 2.10-1.90 (m, 1H); 13 C NMR (DMSO-d ) 8 136.6
6 (C),
136.4 (C), 134.3 (C), 131.5 (CH), 130.7 (CH), 130.5 (CH), 130.2 (CH), 127.9 (CH),
127.7 (CH),
125.6 (CH), 59.0 (CH), 33.3 (CH 2 ), 29.0 (CH2 ), 27.0 (CH ); El MS m/z (relative intensity)
2 223 (M+,
100), 132 (15), 131 (51), 130 (77), 129 (34), 128 (25), 119 (38), 118 (69), 115 (37), 106
(20), 105
(19), 104 (59), 103 (24), 94 (37), 93 (83), 92 (17), 91 (52),78 (32), 77 (60). Analysis
calculated for
C16H18 CIN: C, 73.98; H, 6.98; N, 5.39; Cl, 13.65. Found: C, 73.97; H, 7.04; N, 5.39; Cl,
13.86.

N-(2-Indanylaniline: 30 (Table I, entry 13)

Q- Ph

HCI salt, a white solid that turned tan on standing, mp 180-182 'C (EtOAc/MeOH) (lit31
175-180 0 C).
FT-IR (KBr) 2906 (m), 2851 (m), 2722 (m), 2602 (m), 2473 (m), 1590 (m), 1485 (s), 1435
(s), 1037
(m), 997 (m), 754 (s), 697 (s), 633 (m), 594 (m), 520 (m), 498 (m), 463 (m),
401 (m) cm -1; IH NMR
(DMSO-d 6 ) 5 11.4 (bs, 1H), 7.68 (d, J = 7.8 Hz, 2H), 7.55 (dd, J = 7.8, 7.4 Hz, 2H),
7.45 (t, 1H, J =
7.4 Hz) 7.30-7.10 (m, 4H), 4.43 (q, J = 7.6 Hz, 1H), 3.33 (dd, J = 16.0, 7.6 Hz, 2H),
3.17 (dd, J =
16.0, 7.6 Hz, 2H); 13 C NMR (DMSO-d 6 ) 8 141.2 (C), 138.0 (C), 131.6 (CH), 130.2
(CH), 128.7
(CH), 126.3 (CH), 124.9 (CH), 62.5 (CH), 37.4 (CH2); El MS n/z (relative intensity)
209 (M+, 74),
116 (38), 106 (22), 104 (100), 91(21), 77 (45), 51(16). Analysis calculated for C15H
16 CIN: C, 73.31;
H, 6.56; N, 5.70; Cl, 14.45. Found: C, 73.30; H, 6.57; N, 5.70; Cl, 13.53.
(01996 American Chemical Society Journal Of Organic Chemistry V61 Page 3849 Abdel-Magid Supplemental Page 5

N-Benzyl-4-aminocyclohexanone ethylene ketal: (Table I, entry 14)

NH- CH 2 -Ph

<- 0

Oxalate salt: a white solid, mp 245-246 oC (MeOH). FT-IR (free base, neat): 3062 (w), 3026 (w), 2939
(s), 2879 (s), 1449 (m), 1375 (m), 1337 (w), 1243 (w), 1103 (s), 1034 (m), 921 (m), 741 (m), 701
(m), 664 (m); 1H NMR (free base, CDCl 3 ) 8 7.35-7.19 (m, 5H), 3.91 (s, 4H), 3.79 (s,
2H), 2.64-2.54
(m, 1H), 1.96-1.84 (m, 2H), 1.81-1.70 (m, 2H), 1.59-1.40 (m, 4H), 1.22 (bs, 1H); 13 C NMR (free
base, CDCl 3 ) 8 140.9 (C), 128.3 (CH), 128.0 (CH), 126.8 (CH), 108.7 (C), 64.19 (CH ), 64.17
2
(CH 2 ), 54.3 (CH), 51.2 (CH 2 ), 32.8 (CH 2 ), 30.2 (CH2 ); El MS m/z (relative intensity) 247 (M+,
2),
146 (7), 133 (7), 132 (12), 118 (2), 106 (7), 102 (7), 101 (100), 99 (6), 91 (62), 65 (14),
57 (11).
Analysis calculated for C1 7H2 3 NO 6 : C, 60.52; H, 6.87; N, 4.15. Found: C, 60.45; H, 6.88; N, 4.11.

-CyclobutyL-4-aminocy-clohexanone-ethylene ketal: (Table I, entry 15)

HCI salt: a white solid, mp 207-209 'C (EtOAc/MeOH). FT-IR (KBr) 3445 (s), 2956 (vs), 2805
(s),
2725 (s), 2531 (m), 2435 (m), 1450 (s), 1368 (m), 1102 (vs), 1036 (m), 932 (m) cm- 1 1
; H NMR
(CDCl3) 8 9.70 (bs, 1H), 3.92 (s, 4H), 3.85-3.70 (m, 1H), 3.10-2.90 (m, 1H), 2.70-2.55
(m, 2H),
2.40-2.15 (m, 4H), 2.05-1.75 (m, 6H), 1.65-1.50 (m, 2H); 13 C NMR (CDC13) 8 106.7 (C), 64.3
(CH2), 64.2 (CH2), 54.4 (CH), 49.4 (CH), 32.8 (CH2), 27.2 (CH2), 26.2 (CH2), 15.7 (CH2);
El MS
m/z (relative intensities) 211 (M+, 3), 183 (62), 138 (100), 101 (96), 69 (86), 41 (74). Analysis
calculated for: C12H22CIN0 2 : C, 58.17; H, 8.95; N, 5.65; Cl, 14.31. Found: C, 58.30; H, 8.97;
N,
5.60; Cl, 14.60.
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4-(1-Piperidinyl) cyclohexanone ethylene ketal: (Table I, entry 16)

of'P ND

HCI salt: a white solid, mp 237-239 OC (EtOAc/MeOH). FT-IR (KBr) 3555 (m), 3433 (m), 2931 (s),
2878 (m), 2652 (s), 2545 (m), 1640 (w), 1454 (m), 1112 (s), 1031 (w), 943 (m)
cm- 1 ; 1H NMR
(CDCl 3 ) 8 11.58 (bs, 1H), 3.99-3.90 (m, 4H), 3.41 (bd, J = 11.4 Hz, 2H), 3.14 (bt, J
= 11.9 Hz, 1H),
2.90-2.74 (m, 2H), 2.42-2.30 (m, 5H), 1.94-1.60 (m, 8H), 1.48-1.34 (m, 13C
1H); NMR (CDC13 ) 8
106.6 (C), 64.5 (CH 2 ), 64.2 (CH 2 ), 64.1 (CH), 49.6 (CH ), 33.1
2 (CH 2 ), 23.2 (CH 2 ), 22.6 (CH 2 ),
22.3 (CH 2 ); El MS m/z (relative intensity) 225 (M+, 11), 125 (14), 124 (85), 111 (23),
110 (18), 101
(100), 96 (23), 84 (13). Analysis calculated for C13H2 CIN0 : C, 59.64; H, 9.24;
4 2 N, 5.35; Cl, 13.54.
Found: C, 59.30; H, 9.04; N, 5.32; Cl, 13.38.

1-(4 -Ethylen-edioxycyohexy)-4-phenylpipazine; (Table I, entry 17)

N-Ph

Free base: light tan solid, mp 111-112 'C (hexane). FT-IR (KBr) 2949 (m), 2825 (m),
1601 (s), 1506
(s), 1283 (m), 1235 (s), 1145 (s), 1100 (s), 999 (m), 926 (s), 758
(s), 690 (m) cm- 1 ; 1H NMR (CDCl 3 )
8 7.26 (dd, J = 7.9, 7.3 Hz, 2H), 6.93 (d, J = 7.9 Hz, 2H), 6.85 (dd, J = 7.9,
7.3 Hz, 1H), 3.94 (s,
4H), 3.21-3.18 (m, 4H), 2.75-2.72 (m, 4H), 2.45-2.39 (m, 1H), 1.90-1.80
(m, 4H), 1.70-1.50 (m,
4H); 13 C NMR (CDCl 3 ) 8,151.3 (C), 128.9 (CH), 119.5 (CH), 115.9 (CH), 108.4 (C), 64.2,
(CH 2 ),
64.1 (CH 2 ), 61.8 (CH), 49.5 (CH 2 ), 49.0 (CH 2 ), 33.6 (CH ), 25.4 (CH ); El MS
2 2 m/z (relative
intensity) 302 (M+, 40), 259 (1), 201 (24), 173 (8), 132 (21), 120 (8), 119 (9), 105 (16),
104 (17), 101
(100), 91 (5), 86 (9), 77 (14). Analysis calculated for C H N 0 : C,71.49; H,
18 26 2 2 8.67; N, 9.26.
Found: C, 71.44; H, 8.69; N, 9.27.
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N-14-Ethylenedioxycyclohexyl)-1-amino-2.2-dimethoxvethane: (Table I, entry 18)

ORt

Oxalate salt: a tan solid, mp 169-170 oC (decpn.) (EtOAc/MeOH). FT-IR (KBr) 2976 (m), 2935 (m),
2816 (m), 2787 (m), 1759 (m), 1719, (m), 1717 (m), 1645 (m), 1403 (m), 1134 (s), 1104 (s), 1074

(s), 1038 (s), 950 (m), 721 (s), 497 (s) cm- 1; 1H NMR (CDCl 3 ) 8 8.3 (bs, 3H), 4.58 (t, J = 5.6 Hz,

1H), 3.93 (s, 4H), 3.75-3.65 (m, 2H), 3.60-3.50 (m, 2H), 2.74 (d, J = 5.6 Hz, 2H), 2.60-2.50 (m,

1H), 1.90-1.70 (m, 4H), 1.60-1.40 (m, 4H), 1.21 (t, J = 7.0 Hz, 6H); 13 C
NMR (CDCl 3 ) 8 108.5
(C), 102 (CH), 64.1 (CH 2 ), 62.1 (CH 2 ), 54.9 (CH), 49.4 (CH 2 ), 43.2 (CH 2 ), 32.8 (CH 2 ), 30.0
(CH 2 ), 15.2 (CH 3 ); El MS n/z (relative intensity) 229 (14), 228 (M-OC2H5, 17), 171 (11), 170 (96),

141 (39), 108 (23), 103 (100), 101 (26), 100 (10), 99 (20), 97 (48), 86 (14), 75 (70). Analysis

calculated for C16 H29 NO 8 : C, 52.88; H, 8.04; N, 3.85. Found: C, 52.69; H, 8.05; N, 3.77.

N-(2-Propyl)-3(-aminoandrostane-17-J-ol: (Table 1, entry 21)

Me OH
- H
Me

Free base: a white solid, mp 107-109 oC (hexane). FT-IR (KBr) 3425 (s), 3167 (s), 2925 (vs), 2847
(s), 1639 (w), 1576 (m), 1447 (m), 1124 (w), 1079 (m), 845 (w), 799 (w) cm-1; IH NMR (CD 0D) 8
3

3.55 (t, J = 8.6 Hz, 1H), 3.00-2.85 (m and sept., J = 6.2 Hz, 2H), 2.05-1.90 (m, 1H), 1.85-1.75 (m,

1H), 1.75-1.55 (m, 5H), 1.55-1.35 (m, 5H), 1.35-1.10 (m, 6H), 1.04 (d, J = 6.2 Hz, 6H), 1.00-0.90

(m, 3H), 0.85 (s, 3H), 0.80-0.75 (m, IH), 0.72 (s, 3H); 13 C
NMR (CD 3 0D) 8 82.5 (CH), 55.9 (CH),
52.5 (CH), 49.8 (CH), 45.9 (CH), 44.2 (C), 41.1 (CH), 38.1 (CH 2 ), 37.4 (C), 36.9 (CH), 33.8
(CH 2 ), 33.5 (CH 2 ), 32.9 (CH2 ), 30.7 (CH 2 ), 29.9 (CH 2 ), 26.3 (CH2 ), 24.4 (CH 2 ), 22.8 (CH 3 ), 21.6

(CH 2 ), 12.1 (CH 3 ), 11.8 (CH 3 ); El MS n/z (relative intensity) 333 (M+, 9), 319 (9), 318 (35), 124
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8 (7 53bfrg
(38), 98 (100), 79 (10), 70 (13). Analysis calculated for C22 H 39 NO: C, 79.22; H, 11.79; N, 4.20.
Found: C, 79.44; H, 12.02; N, 3.94.

N-(2-Propyl)-30-aminoandrostane-17-0-ol: (Table 1, entry 21)

Me OH
**-H
Me

Free base: a white solid, mp 203-205 oC (EtOAc). FT-IR (KBr) 3389 (s), 2927 (vs), 2848 (s), 1445
(m), 1379 (m), 1139 (w), 1051 (m) cm- 1; 1H NMR (CD 3 0D) 8 3.55 (t, J = 8.6 Hz, 1H), 2.99 (sept.,
J
= 6.3 Hz, 1H), 2.65-2.50 (m, 1H), 2.05-1.91 (m, 1H), 1.85-1.65 (m, 4H), 1.65-1.35 (m, 6H), 1.35-
1.10 (m, 8 H), 1.04 (d, J = 6.3 Hz, 6H), 1.00-0.90 (m, 3H), 0.84 (s, 3H), 0.72 (s, 3H); 13 C NMR
(CD 3 0D) 8 82.5 (CH), 56.1 (CH), 54.9 (CH), 52.4 (CH), 47.0 (CH), 45.5 (CH), 44.1 (C), 38.9

(CH 2 ), 38.1 (CH 2 ), 37.2 (C), 37.0 (CH), 36.5 (CH2 ), 32.9 (CH2 ), 30.7 (CH ), 30.0 (CH2), 29.7
2
(CH 2 ), 24.3 (CH2 ), 22.8 (CH 3 ), 22.7 (CH3 ), 21.9 (CH 2 ), 12.8 (CH ), 11.7 (CH ); El MS n/z
3 3
(relative intensity) 333 (M+, 19), 319 (24), 318 (100), 124 (43), 98 (94), 79 (8), 70 (11).

DicVcloheptylamine: (Table I, entries 22 & 23)

HCI salt, white crystalline solid, mp oC (EtOAc/MeOH). 1l NMR (CDCl 3 ) 8 9.03 (bs, 1H), 3.23-3.09
(m, 2H), 2.31-2.15 (m, 4H), 2.02-1.73 (m, 8H), 1.56 (bs, 8H), 1.48-1.31 (m, 4H); 13 C NMR
(CDCl 3 ) 8 57.0 (CH), 31.0 (CH2 ), 27.2 (CH2 ), 24.1 (CH 2 ); EI-MS n/z (relative intensity) 209 (M+,

10), 166 (27), 153 (12), 152 (100), 124 (20), 114 (10), 112 (7), 97 (6), 96 (7), 82 (12), 70 (13), 56
(73), 55 (57).
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N-Benzvl-endo-2-aminonorbornane: (Table I, entry 24)

44H
NH-CH 2 Ph

HCI salt, white solid, mp 237-239 oC (EtOAc/MeOH). FT-IR (free base, neat) 3062 (w), 3028 (w),
2974 (s), 2867 (m), 2812 (m), 1496 (w), 1452 (m), 1443 (m), 1304 (w), 1164 (w), 1128 (w), 1105
(w), 736 (m), 698 (m) cm- 1 ; 1H NMR (free base, CDCl 3 ) 8 7.37-7.10 (m, 5H), 3.70 (dd, I = 28.8,

12.8 Hz, 2H), 3.08-3.04 (m, 1H), 2.31 (bs, 1H), 2.14 (bs, IH), 1.93-1.86 (m, 1H), 1.76-1.70 (m,
1H), 1.56-1.48 (m, 1H), 1.37-1.18 (m, 5H), 0.70-0.65 (m, IH); 1 3 C NMR (free base, CDCl ) 8 140.7
3

(C), 128.4 (CH), 128.3 (CH), 126.9 (CH), 59.0 (CH), 52.7, (CH 2 ), 39.4, (CH2), 28.2, (CH2), 36.8,
(CH), 30.2, (CH 2 ), 20.7, (CH 2 ); El MS m/z (relative intensity) 201 (M+, 8), 172 (12), 146 (7), 133
(8), 132 (17), 120 (10), 110 (28), 106 (8), 92 (12), 91 (100), 67 (10), 65 (24). Analysis calculated for

C14H20CIN: C, 70.72; H, 8.48; N, 5.89; Cl, 14.91. Found: C, 70.55; H, 8.48; N, 5.73; Cl, 15.17.

N-Phenyl-2-aminonorbornane: (Table I, entries 25 & 26)

46H
NH-Ph

HCI salt, a white crystalline solid turned light green on storage, mp 188-190 oC (EtOAc / MeOH). FT-IR
(KBr) 3419(s), 2962(s), 2876(s), 2743(s), 2636(s), 2528(m), 2469(m), 1566(m), 1494(s), 1413(m),
741(m), 692(s) cm- 1; 1H NMR (CD 3 0D) 8 7.65 (m, 5H), 4.95 (bs, 2H),
3.97 (m, 1H), 2.47 (m, 2H),
2.19 (m, 1H), 1.96 (m, 1H), 1.80 (m, 5H), 1.40 (m, 1H); 1 3 C NMR (CD 0D) 137.0 (C),
3 a131.6
(CH), 130.7 (CH), 124.0 (CH), 66.0 (CH), 40.0 (CH), 38.9 (CH2), 38.0 (CH), 34.6 (CH ), 30.5
2
(CH 2 ), 22.5 (CH2 ); CI MS m/z (relative intensity) 188 (MH+, 100), 187 (82), 132(10), 119 (34), 118
(11), 106 (20), 95 (52), 94 (31), 93 (39), 85 (35), 83 (51). Analysis calculated for C 3H CIN: C,
1 18
69.79; H, 8.11; N, 6.26; Cl, 15.58. Found: C, 69.78; H, 8.25; N, 5.99; Cl, 15.89.
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NN-Diethyl endo -2-aminonorbornane: (Tablel, entry 27)

4 H
N(C 2 H 5 ) 2

HCI salt, a white solid, mp 157-159 'C (EtOAc/hexane). FT-IR (neat) 2959 (vs), 2866 (s), 2805 (s),
1452 (m), 1365 (m), 1358 (m), 1287 (m), 1203 (m), 1167 (w), 1052 (m), 776 (m) cm- 1 ; 1H NMR
(CDC1 3 ) 8 2.71-2.65 (m, 1H), 2.65-2.52 (m, 4H), 2.23 (s, 1H), 2.14 (s, 1H), 1.78-1.51 (m, 2H),
1.50-1.40 (m, 1H), 1.38-1.20 (m, 4H), 0.94 (t, J = 7.0 Hz, 6H), 0.91-0.86 (m, 1H); 13 C NMR
(CDC13 ) 8 62.8 (CH), 43.3 (CH2 ), 39.5 (CH), 37.9 (CH2), 36.8 (CH 2 ), 30.7 (CH 2 ), 21.0 (CH2 ), 11.7

(CH 3 ); El MS m/z (relative intensity) 167 (M+, 44), 166 (11), 152 (57), 139 (11), 138 (71), 126 (47),
124 (19), 112 (19), 110 (37), 99 (26), 98 (37), 95 (23), 86 (100), 84 (25), 82 (15), 72 (38), 71 (27), 70
(18), 68 (17), 67 (55), 58 (53), 56 (70). Accurate mass calculated for Cl1 H 22 N+ (MH+): 168.1752.
Found: 168.1747+ 0.0017, difference: 3.0 ppm.

endo-N-Benzyl 3-aminotropane: (Table I, entry 28 and Table V, entry 10)

N- CH 3
H
NHCH 2 Ph

Oxalate salt: a white solid, mp 169-172 (dec.) (MeOH). FT-IR (KBr) 3491 (m), 3028 (m), 1605 (s),
1313 (m), 758 (m) cm-1; 1H NMR (D2 0) 8 7.51 (bs, 5H), 4.37 (bs, 2H), 4.05-3.95 (m, 2H), 3.62-
3.57 (bt, J = 7.8 Hz, 1H), 2.80 (s, 3H), 2.68-2.41 (m, 4H), 2.30-2.13 (m, 4H); 13C NMR (D2 0) 8

175.6 (C), 133.0 (CH), 132.7 (CH), 132.6 (C), 132.2 (CH), 63.6 (CH), 53.0 (CH 2 ), 48.3 (CH), 41.3
(CH 3 ), 34.2 (CH2 ), 26.5 (CH 2 ); FAB MS m/z 231 (MH+). El MS m/z (relative intensity) 230 (M+, 2),
139 (75), 91 (45), 82 (100), 42 (38). Analysis calculated for C 1 7 H24 N2 0 4 * 0.5 H2 0: C, 61.99; H,
7.65; N, 8.50. Found: C, 62.17; H, 7.48; N, 8.51.
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endo-N-Phenyl-3-amino tropane: (Table I, entry 29)

N. CH 3
H
NHPh
Oxalate salt: a white solid, mp 177-178 0 C (dec.) (EtOH). FT-IR (KBr) 3319 (m), 2964 (m), 2850
(m),
2576 (m), 2504 (m), 2362 (w), 1938 (w), 1722 (m), 1627 (s), 1599 (s), 1495 (m), 1329 (m), 1208 (s),
762 (m), 700 (m), 512 (w) cm- 1; 1H NMR (CD 3 0D) 8 7.12 (dd, J = 7.8, 7.3, 2H), 6.65 (t, J = 7.3 Hz,
1H), 6.60 (d, J = 7.8 Hz, 2H), 3.90-3.80 (m, 2H), 3.70-3.60 (m, 1H), 2.77 (s, 3H),
2.55-2.35 (m,
4H), 2.29-2.13 (m, 4H); 13C NMR (CD 3 0D) 8 166.8 (C), 148.7 (C), 130.2 (CH), 118.5 (CH), 114.2

(CH), 64.2 (CH), 43.9 (CH 3 ), 39.5 (CH), 35.4 (CH 2 ), 24.5 (CH2); El Ms m/z (relative intensity)
216
(M+, 60), 124 (100), 97 (60), 82 (80), 44, (60), 28 (50); Accurate mass
calculated for C14H 2 0 N 2 :
216.1626. Found: 216.1627.

exo- 3 -(1-PiperidinyDtropane: (Table I, entry 30 and Table 5, entry 9)

N' CH 3

H
Oxalate salt: a white solid, mp 200-202 'C (dec.) (EtOAc/MeOH). FT-IR (KBr) 3437 (m), 2949
(m),
1
1627 (s), 1450 (m), 769 (m) cm- ; H NMR (CD 3 0D) 8 4.00-3.90 (m, 2H), 3.60-3.45 (m, 1H),
1
3.40-
3.10 (m, 4H), 2.69 (s, 3H), 2.65-2.50 (m, 2H), 2.45-2.30 (m, 4H), 2.10-2.00 (m, 2H),
1.90-1.80 (m,
4H), 1.70-1.55 (m, 2H); 13 C NMR (CD 3 0D) 8 169.4 (C), 63.5 (CH ), 57.1 (CH), 52.2
3 (CH2 ), 38.9
(CH), 32.2 (CH 2 ), 24.8 (CH 2 ), 24.5 (CH 2 ), 22.8 (CH2 ); El MS m/z (relative intensity)
208 (M+, 80)
125 (40) 97 (100) 82 (50). Accurate mass calculated for C13H24 N2: 208.1939. Found: 208.1937. Free
amine 1 H NMR (CDCl 3 ) 8 3.19 (m, 2H), 2.61 (m, 1H), 2.47 (m, 4H), 2.28 (s, 3H), 1.97
(m, 2H),
1.74 (m, 2H), 1.55 (m, 8H), 1.41 (m, 2H). 13 C NMR 8 60.5 (CH), 55.0 (CH), 50.1 (CH 2 ), 39.1
(CH 3 ), 31.9 (CH 2 ), 26.7 (CH 2 ), 26.5 (CH ), 24.7 (CH ).
2 2
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N-(2-Heptyl) cyclohexyl amine: (Table I, entry 31)

CH 3

CH3 H

Oxalate salt: a white solid, mp 146-147 oC (MeOH). FT-IR (KBr) 3084 (m), 2936 (vs), 2861 (s), 2508
(w), 2427 (w), 1742 (s), 1647 (vs), 1583 (m), 1456 (m), 1408 (s), 1284 (s), 1192 (m), 726 (m) cm- 1 ;

IH NMR (Oxalate, CDCl 3 ) 8 10.85 (bs, 1H), 8.97 (bs, 1H), 8.85 (bs, 1H), 3.40-3.28 (m, 1H), 3.22-

3.09 (m, 1H), 2.08-1.94 (m, 2H) 1.84-1.70 (m, 3H), 1.66 (d, J = 12.2 Hz, 1H), 1.55-1.08 (m + d,

J = 6.4 Hz, 15H), 0.86 (t, J = 6.7 Hz, 3H); (free base, CDCl3 ) 8 2.86-2.78 (m, 1H), 2.61-2.52 (m,

1H), 1.97-1.83 (m, 2H), 1.78-1.68 (m, 2H), 1.65-1.58 (m, 1H), 1.52-1.40 (m, 1H), 1.39-1.05 (m,

13H), 1.06 (d, J = 6.2 Hz, 3H), 0.89 (t, J = 6.9 Hz, 3H); 13 C NMR (Oxalate, CDC13 ) 8 163.3 (C),
53.7 (CH), 50.5 (CH), 32.9 (CH 2 ), 31.5 (CH2 ), 29.6 (CH2), 28.7 (CH ), 25.5 (CH ), 25.1 (CH ),
2 2 2
24.72 (CH 2 ), 24.67 (CH 2 ), 22.5 (CH 3 ), 15.7 (CH 3 ); El MS n/z (relative intensity) 197 (M+, 1), 182

(6), 154 (13), 127 (10), 126 (100), 70 (8), 56 (21), 55 (22). Analysis calculated for C1 H2 NO : C,
5 9 4
62.69; H, 10.17; N, 4.67. Found: C, 62.51; H, 10.26; N, 4.82.

N-(2-Heptyl) aniline: (Table I, entry 32)

CHz NH-Ph
CH 3

Oxalate salt: a white solid, mp 135-136 oC (MeOH). FT-IR (KBr) 3410 (m), 2938 (m), 2924 (s), 2863

(s), 2656 (s), 2604 (s), 2662 (m), 1434 (m), 1396 (m), 1266 (m), 1114 (s), 1072 (m), 928 (m); 1H
NMR (CD 3 0D) 8 7.50-7.41 (m, 2H), 7.38-7.30 (m, 3H), 3.57 (bs, 1H), 1.82-1.70 (m, 1H), 1.62-

1.50 (m, 1H), 1.50-1.30 (m, 6H), 1.26 (d, J = 5.8 Hz, 3H), 0.89 (t, J = 6.4 Hz, 3H); 13 C
NMR
(CD 3 0D) 8 165.8 (C), 138.1 (C), 131.0 (CH), 128.4 (CH), 123.0 (CH), 58.4 (CH), 34.5 (CH ), 32.7
2

(CH 2 ), 26.3 (CH 2 ), 23.4 (CH2 ), 17.2 (CH3 ), 14.3 (CH 3 ); El MS n/z (relative intensity) 191 (M+, 24),
176 (13), 121 (21), 120 (100), 118 (10), 106 (10), 91 (5), 92 (5), 77 (17). Analysis calculated for
C1 5 H2 3 NO 4 : C, 64.03; H, 8.24; N, 4.98. Found: C, 63,58; H, 8.38; N, 5.31.
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1-(2-Heptyl) piperidine: (Table I, entries 34 & 35)

CHz
N
CH3

HCI salt: a white solid, mp 160-161 oC (EtOAc/MeOH). FT-IR (KBr) 3414 (m), 3277 (m), 2939 (s),
2863 (s), 1716 (m), 1632 (m), 1548 (s), 1455 (m), 1404 (m), 1217 (s), 721 (s) cm- 1; 1H NMR (CDCl )
3
8 10.84 (bs, 1H), 2.85-2.83 (m, 2H), 2.68 (bs, 1H), 2.40 (bs, 2H), 1.92-1.77 (m, 2H), 1.62-1.54 (m,
1H), 1.37 (d, J = 11.8 Hz, 3H), 1.1-0.80 (m, 11H), 0.38-0.37 (m, 3H); 13 CNMR (CDCl 3 ) 8 62.1
(CH), 49.3 (CH 2 ), 48.5 (CH 2 ), 31.0 (CH 2 ), 30.2 (CH2), 25.8 (CH2), 22.5 (CH 2 ), 22.4 (CH2), 13.6
(CH 3 ), 13.4 (CH3 ); El MS n/z (relative intensity) 183 (M+,-5), 168 (23), 113 (21), 112 (100), 84 (8),
69 (8), 56 (14), 55 (13). Analysis calculated for C1 2 H26 CIN: C, 65.57; H, 11.92; N, 6.37; Cl, 16.13.
Found: C, 64.50; H, 12.07; N, 6.79; Cl, 16.16.

N-(2-Heptyl) diethyl amine: (Table I, entry 36)

CH3 N- CH 3
CH 3 '- CH 3

HCl salt: a white solid, mp 56-58 'C (EtOAc). FT-IR (KBr) 3504 (s), 3433 (m), 2947 (vs), 2728 (m),
2688 (vs), 2533 (m), 2493 (m), 1620 (m), 1472 (vs), 1430 (m), 1400 (s), 1177 (m), 1120 (m), 1096

(m), 1026 (s), 544 (vs) cm- 1; 1H NMR (CDCl 3 ) 8 11.45 (bs, 1H), 3.47-3.39 (m, 1H), 3.36-3.08 (m,

4H), 2.21 (bs, 1H), 2.04-1.97 (m, 1H), 1.51 (t, J = 7.3 Hz, 6H), 1.49 (d, J = 6.6 Hz, 3H), 1.45-1.32
(m, 6H), 0.90 (t, J = 6.0 Hz, 3H); 13 CNMR (CDCl 3 ) 8 57.2 (CH), 44.3 (CH 2 ), 31.2 (CH 2 ), 30.2
(CH 2 ), 25.8 (CH2 ), 22.2 (CH 2 ), 13.7 (CH 3 ), 13.5 (CH 3 ), 9.9 (CH3 ); El MS n/z (relative intensity)
171 (M+, 2), 156 (10), 101 (7), 100 (100), 72 (13), 58 (12). Analysis calculated for C1 1 H26 CIN: C,
63.58; H, 12.61; N, 6.74; Cl, 17.06. Found: C, 63.29; H, 12.79; N, 6.68; Cl, 16.92.

N-1-Cyclohexylethyl)benzylamine: (Table I, entries 37, 44)

NH- CH 2 -Ph

CH 3
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HCI salt: a white solid, mp 209-210 oC (EtOAc/MeOH). FT-IR (KBr) 2970 (s), 2927 (s), 2852 (s),
2807 (s), 2702 (m), 2574 (m), 2492 (m), 1579 (m), 1454 (m), 1307 (m), 740 (m), 698 (m) cm- 1 ; 1H
NMR (free base, CDCl 3 ) 8 7.40 (m, 5H), 3.90 (d, J = 13.0 Hz, 1H), 3.70 (d, J = 13.0 Hz, 1H), 2.50

(q, J = 6.0 Hz, 1H), 1.80-1.62 (m, 6H), 1.42-1.05 (m, 6H), 1.01 (d, J = 3.0 Hz, 3H); 13 C NMR (free
base, CDCl 3 ) 8 141.1 (C), 128.3 (CH), 128.1 (CH), 126.7 (CH), 57.0 (CH), 51.5 (CH2 ), 42.9 (CH),

29.8 (CH 2 ), 28.0 (CH 2 ), 26.8 (CH 2 ), 26.7 (CH 2 ), 26.5 (CH 2 ), 25.6 (CH 2 ), 16.7 (CH 3 ); CI MS
(NH 3 ) m/z (relative intensity) 218 (MH*, 97), 135 (11), 134 (100), 108 (33), 106 (19), 91 (80).
Analysis calculated for C15H2 4 CIN: C, 70.98; H, 9.53; N, 5.52; Cl, 13.97. Found: C, 70.91; H, 9.55;
N, 5.51; Cl, 13.95.

N-(3-Phenyl-2-propyl)aniline: (Table I, entry 38)

PH
-P

HCI salt: White solid turned greenish on storage, mp 150-152 oC (EtOAc/MeOH). FT-IR (KBr) 3414
(m), 2930 (s)), 2763 (vs), 2691 (vs), 2609 (vs), 2475 (s), 1574 (s), 1495 (s), 1378 (m), 1070 (m), 742

(vs), 696 (vs), 499 (m) cm- 1 ; 1H NMR (DMSO-d 6 ) 8 11.25 (bs, 1H), 7.62-7.50 (m, 4H), 7.43-7.22

(m, 6H), 3.87-3.80 (m, 1H), 3.27 (dd, J= 12.9, 3.5 Hz, 1H), 2.76 (dd, J= 12.9, 10.7 Hz, 1H), 1.09

(d, J = 6.4 Hz, 3H); 13 C NMR (DMSO-d 6 ) 8 138.6 (C), 137.2 (C), 131.4 (CH), 130.9 (CH), 130.3
(CH), 128.4 (CH), 125.2 (CH), 59.7 (CH), 40.3 (CH2 ), 17.1 (CH 3 ); EI-MS n/z (relative intensity)

211 (M+, 4), 121 (10), 120 (100), 91 (19), 77 (15), 65 (12). Analysis calculated for C H CIN: C,
15 18

72.72; H, 7.32; N, 5.65; Cl, 14.31. Found: C, 72.51; H, 7.26; N, 5.64; Cl, 14.46.

N-(4-Heptyl~pronargylamine: (Table I, entry 39)

---
CH 2

HCI salt: colorless crystals, mp 151-153 'C (EtOAc). FT-IR (KBr) 3229 (m), 2960 (s), 2933 (s), 2873
(s), 2780 (s), 2682(s), 2584 (m), 1576 (m), 1461 (s), 1428 (s), 1379 (m), 1030 (m), 737 (s), 696 (s)

cm-1; 1 H NMR (CDCl3) 8 9.80 (bs, 2H), 3.95-3.85 (m, 2H), 3.40 (quintet, J = 5.9 Hz, 1H), 2.55 (t, J
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= 2.5 Hz, 1H), 1.84-1.74 (m, 4H), 1.54-1.46 (m, 4H), 0.97 (t, J = 7.3 Hz, 6 H); 1 3 C NMR (CDC1 ) 5
3
77.5 (C), 73.0 (CH), 56.1 (CH), 33.6 (CH2), 31.7 (CH2), 18.2 (CH2), 13.7 (CH3); CI MS (relative

intensity) 154 (100, MH*), 91 (10). Analysis calculated for C10 H20 CIN: C, 63.31; H, 10.63; N, 7.38;
Cl, 18.69. Found: C, 63.28; H, 10.87; N, 7.31; Cl, 18.88.

N-(Benzvl)-1-phenvlethvlamine: (Table I, entry 40)

Ph Y Ph
CH3

HCI salt: a white solid, mp 179-181 oC (EtOAc/MeOH). FT-IR (KBr) 3429(m), 2937(s), 2832(s),
2792(s), 2 743(s), 2655(m), 1582(m), 1497(m), 1457(s), 1414(w), 1380(w), 764(m), 699(s); IH NMR
(DMSO-d6/CDCl 3 ) 8 10.55 (bs, 1H), 10.10 (bs, 1H), 7.74 (d, J = 7.2 Hz, 1H), 7.56 (d, J = 2.4 Hz,

2H), 7.48-7.17 (m, 6H), 4.39-4.38 (m, 1H) 4.02, 3.77 (ABq, J = 13.2 Hz, 2H), 1.72 (d, J = 6.7 Hz,
3H); 13 C NMR (DMSO-d6/CDCl 3 ) 8 137.3 (C), 131.8 (C), 130.2 (CH), 129.1 (CH), 128.8 (CH),

128.7 (CH), 128.4 (CH), 128.1 (CH), 57.3 (CH), 48.4 (CH ), 19.9 (CH ); CI MS m/z (relative
2 3
intensity) 212 (MH+, 62), 210 (4), 197 (7), 196 (42), 134 (18), 133 (9), 108 (16), 106 (14), 105 (100),
91(34).

N-Benzylcyclohexvlamine: (Table I, entry 42)

N'Ph
H

HCI salt: a white solid, mp >240 oC (EtOAc/MeOH). FT-IR (KBr) 2934 (vs), 2856 (s), 2788 (s), 2735
(s), 2639 (m), 2584 (m), 2435 (m), 1590 (m), 1455 (s), 996 (w), 740 (m), 693 (s), 504 (m) cm-1 1
H
NMR (DMSO-d 6 ) 8 9.44 (bs, 2H), 7.65-7.62 (m, 2H), 7.46-7.37 (m, 3H), 4.12 (s, 2H), 2.98-2.83

(m, 1H), 2.20-2.08 (m, 2H), 1.81-1.70 (m, 2H), 1.65-1.56 (m, 1H), 1.53-1.39 (m, 2H), 1.28-1.02
(m, 3H); 13 C NMR (DMSO-d 6 ) 8 134.1 (C), 131.8 (CH), 130.5 (CH), 130.3 (CH), 57.5 (CH), 48.5

(CH 2 ), 30.0 (CH2 ), 26.5 (CH 2 ), 25.7 (CH2 ); EI-MS m/z (relative intensity) 189 (M+, 17), 160 (4), 147
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(8), 146 (67) 132 (8), 106 (5), 92 (9), 91 (100), 65 (17). Analysis calculated for C13H20CIN:
C, 69.16;
H, 8.93; N, 6.20; Cl, 15.70. Found: C, 69.23; H, 8.89; N, 6.13; Cl, 15.92.

N-Benzvlalanine methyl ester: (Table I, entry 47)

CO2CH3
CH 2 - NH
CH 3

HCI salt: a white solid, mp 162-163 oC (EtOAc/MeOH). FT-IR (KBr) 3431 (m), 2931 (m), 2808 (m),
2729 (s), 2632 (m), 2597 (m), 2597 (m), 2538 (m), 2391 (m), 1742 (s), 1557 (m), 1453
(m), 1453
(m), 1256 (m), 1210 (m), 1142 (m), 1097 (w), 980 (w), 751 (w), 688 (m) cm- 1 ; 1H NMR
(CDCl3): 8
10.6 (bs, 1H), 10.35 (bs, 1H), 7.63 (d, J = 6.9 Hz, 2H), 7.40-7.33 (m, 3H), 4.26, 4.18 (ABq,
J=
13.7 Hz, 2H), 3.78 (s, 3H), 3.69 (q, J = 7.2 Hz, 1H), 1.67 (d, J = 7.2
Hz, 3H); 13 C NMR (CDCl3): 5
169.0 (C), 130.8 (CH), 129.7 (C) 129.5 (CH), 129.0 (CH), 53.2 (CH3), 53.0 (CH), 48.8
(CH2), 14.8
(CH3); El MS n/z (relative intensity) 134 [(M+-CO CH ), 54], 106 (9), 92 (10),
2 3 91 (100), 65 (16).
Analysis calculated for CIIHi6 CINO 2 : C, 57.52; H, 7.02; N, 6.10; Cl, 15.44. Found: C,
57.71; H,
6.80; N, 6.14; Cl, 15.29.

N-Benzvlphenvlglvcine methyl ester: (Table I, entry 49)

CO 2 Me

HCI salt: a white solid, mp 185-186 'C (EtOAc/Hexane). FT-IR (KBr) 3006 (w), 2927 (m),
2802 (m),
2685 (m), 2598 (m), 2551 (m), 1745 (s), 1561 (w), 1457 (m), 1317 (m), 1257 (m),
1171 (m), 757 (w),
730 (w), 700 (m), 509 (w) cm- 1; 1H NMR (CDCl3) 8 11.0 (bs, 1H), 7.62-7.37 (m, 10 H),
4.67-4.64
(d and in, J = 13.8 Hz, 2H), 3.79 (d, J = 13.8 Hz, 1H), 3.71 (s, 3H); 13 C NMR (CDC13)
8 167.9 (C),
130.8 (CH), 130.2 (CH), 129.5 (CH), 129.5 (CH), 129.5 (CH), 129.0 (CH), 128.8 (C), 60.8
(CH),
53.4 (CH3), 48.0(CH2); CI MS n/z 256 (MH*, 32), 196 (100), 91 (53). Analysis calculated
for
C16H1 8 CINO 2 : C, 65.86; H, 6.22; N, 4.80. Found: C, 65.67; H, 6.25; N, 4.73.
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N-(2-ButyDlgycine ethyl ester: (Table I, entry 50)

HO0

CH 3 Ya N- OEt
CH 3

HCI salt: a white solid, mp 128-129 'C (EtOAc/MeOH). FT-IR (KBr) 3416 (w), 2973 (m), 2942
(s),
2785 (m), 2752 (m), 1753 (s), 1578 (w), 1391 (m), 1233 (s), 1066 (m) cm -1; 1H NMR (CDCl ) 8 9.70
3

(bs, 1H), 4.27 (q, J = 7.1 Hz, 2H), 3.87 (dd, Jz = 16.9, J2 = 7.7 Hz, 211), 3.50-3.30 (m, 1H), 2.15-
2.00 (m, 1H), 1.85-1.70 (m, 1H), 1.44 (d, J = 6.3 Hz, 3H), 1.31 (t, J = 7.1 Hz, 3H), 1.02 (t, J = 7.0
Hz, 3H); 13 C NMR (CDCl 3 ) 8 165.8 (C), 62.1 (CH2), 55.8 (CH), 43.9 (CH2), 25.6 (CH2), 15.1
(CH3), 13.8 (CH3), 10.0 (CH3); El MS m/z (relative intensity) 160 (MH+, 1), 130 (76), 86 (62), 70

(25) 56 (100). Analysis calculated for C8HI 8 CINO 2 : C, 49.10; H, 9.27; N, 7.16; Cl, 18.12. Found: C,
49.04; H, 9.23; N, 7.09; Cl, 18.27.

N2 -[(4-Ethylenedioxy)cyclohexvll-Nl-phenylhydrazine: (Table I, entry 51)

H-NH-Ph

Oxalate salt: a light brown solid, mp 169-170 oC (MeOH). FT-IR (KBr) 3434 (m) 3216 (s), 3047 (m),
2934 (s), 2890 (s), 2798 (s), 2700 (s), 1721 (s), 1603 (s), 1408 (s), 1163 (s), 1106 (s), 720 (s), 493 (s)
cm- 1 ; 1H NMR (CD 3 0D) 8 7.40-7.30 (m, 2H), 7.1-7.0 (m, 3H), 3.95 (s, 4H), 3.40-3.30 (m, 1H),
2.2-2.1 (m, 2H), 1.90-1.50 (m, 6H); 13 C NMR (CD3 0D) 8 165.8 (C), 145.6 (C), 130.6 (CH), 124.0
(CH), 117.5 (CH), 108.5 (C), 65.6 (CH 2 ), 65.4 (CH 2 ), 58.8 (CH), 33.5 (CH2 ), 26.7 (CH ); CI MS
2
m/z (relative intensity) 249 (MH+, 100) 141 (35), 120 (12), 94 (20). Analysis calculated for
C16 H 2 2 N2 0 6 : C, 56.80; H, 6.55; N, 8.28. Found: C, 56.62; H, 6.36; N, 8.21. Free base: a yellow
solid that turned dark brown on storage, mp 42-45 'C (hexane/ether); 1H NMR (CDCl ) 8 7.70-7.60 (m,
3

2H), 7.50-7.40 (m, 3H), 4.00 (s, 4H), 3.80-3.65 (m, 1H), 2.30-2.10 (m, 2H), 2.05-1.85 (m, 4H),
1.80-1.65 (m, 2H); 13 C NMR (CDCl 3 ) 8 152.0 (C), 130.2 (CH), 128.8 (CH), 122.0 (CH), 108.2 (C),

74.1 (CH), 64.3 (CH2 ), 32.4 (CH2 ), 28.1 (CH 2 ).

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N2 -cyclohexyl-N1-phenvlhydrazine: (Table I, entry 52)

N-NH-Ph

Free base: a yellow oil turned dark brown on standing. IH NMR (CDCl ) 8 7.66 (dd, Jj = 8.0, J2 = 2.0
3

Hz,.2H), 7.48-7.36 (m, 3H), 3.72-3.61 (m, 1H), 1.99-1.38 (m, 8H), 1.50-1.30 (m, 4H); 13 C
NMR
(CDCl 3 ) 8 152.1 (C), 130.1 (CH), 128.8 (CH), 122.0 (CH), 76.6 (CH), 30.7 (CH 2 ), 25.5 (CH ), 24.2
2
(CH 2 ); ESI-MS: m/z 191 (MH+).

2 cyclohexyll-N1phenylhydrazine: (Table I, entry 53)

H
N-NH-Ph

The crude product, a yellow oil (2.05 g), contained a mixture of the desired product and an unknown by-

prodyct in 69 : 31 ratio. Treatment of this mixture with oxalic acid (1.50 g) in EtOAc and stirring for lh

at rt gave a white solid which was recrystallized from EtOAc to give 1.1 g of product, 37%, mp
142-144
oC. 1H NMR (DMSO-d 6 ) 8 7.13 (m, 2H), 6.88 (d, J = 7.7 Hz, 2H), 6.67 (t, J = 7.3
Hz, IH), 3.04-
2.90 (m, 1H), 1.63-1.50 (m, 1H), 1.41-1.18 (m, 7H), 1.06 (d, J = 6.4 Hz, 3H), 0.86 (t, J =
6.8 Hz,
3H); 1 3 C NMR (DMSO-d 6 ) 5 164.1 (C), 130.4 (CH), 119.8 (CH), 114.7 (CH), 56.3 (CH), 35.0

(CH 2 ), 33.1 (CH 2 ), 26.6 (CH 2 ), 23.8 (CH2 ), 19.1 (CH 3 ), 15.6 (CH ); ESI-MS: m/z 207 (MH+).
3

A -(4-Heptyl)-N1-phenyldiaminoethane: (Table I, entry 55)

Ph-N*- N<
H H
Di HCI salt: a white solid, mp 133-135 oC (EtOAc/MeOH). FT-IR (KBr) 3400 (w), 2960 (s), 2934 (s),
2872 (s) 2769 (s), 2737 (s), 2674 (s), 2562 (s), 2449 (s), 2409 (s), 1473 (s), 720 (s) cm- 1 ; IH NMR
(free base, CDCl3) 8 7.16 (dd, J1 = 7.6, J2 = 7.3 Hz, 2H), 6.68 (t, J = 7.3 Hz, 1H), 6.62 (d, J = 7.6

Hz, 2H), 3.15 (dd, J1 = 6.1, J2 = 5.5 Hz, 2H), 2.83 (dd, J1 = 6.1, J2 = 5.5 Hz, 2H), 2.55-2.45
(m,
1H), 1.50-1.30 (m, 8H), 1.00-0.80 (m, 6H); 13C
NMR (free base, CDCl3) 8 148.6 (C), 129.0 (CH),
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117.2 (CH), 112.9 (CH), 56.6 (CH), 45.5 (CH2 ), 44.0 (CH 2 ), 36.5 (CH2 ), 18.9 (CH 2 ), 14.3 (CH );
3
El MS m/z (relative intensity) 234 (M+, 8), 191 (5), 128 (69), 107 (100), 86 (46), 57 (46). Analysis
calculated for C15H28Cl 2 N2 : C, 58.63; H, 9.18; N, 9.12; Cl, 23.07. Found: C, 58.63; H, 9.30; N,
8.90; Cl, 22.95.

1-rr2-(1-Cyclohexyllethylaminolethyllpiperazine: (Table I, entry 56)

CH 3
0 ,<N N-H

Dioxalate salt: a white solid, mp 203-204 oC (MeOH). FT-IR (free base, neat) 3293 (w), 2925 (s), 2850
(s), 2811 (s), 1448 (m), 1371 (m), 1322 (m), 1265 (m), 1141 (m), 1061 (w), 1017 (w), 776 (w) cm- 1;
1H NMR (free base, CDCl3) 8 2.95-2.80 (m, 3H), 2.80-2.70 (m, 1H), 2.70-2.50 (m, 1H), 2.50-2.30
(m, 8H), 1.80-1.60 (m, 7H), 1.40-1.10 (m, 4H), 1.10 (d, J = 6.7 Hz, 2H); 1H NMR (oxalate, D2 0) 8

3.45-3.05 (m, 8H), 3.00-2.80 (m, 5H), 1.85-1.60 (m, 6H), 1.40-1.05 (m, 8H); 13 C NMR (oxalate,
D 2 0) 8 172.4 (C), 61.6 (CH), 55.1 (CH2), 51.7 (CH2), 45.8 (CH2), 43.5 (CH2), 42.1 (CH), 31.5
(CH2), 29.1 (CH2), 28.3 (CH2), 14.9 (CH3); ESI MS 240 (MII+), 154, 113; El MS m/z (relative

intensity) 223 (1), 222 (3), 156 (4), 140 (11), 100 (34), 99 (100), 70 (24), 69 (14). Accurate mass
calculated for C14H3oN 3+ (M+): 240.2440. Found: 240.2441+ 0.0017, difference: 0.4 ppm.

N-(Cyclohexvlmethyl) benzyl amine: (Table II, entry 1)

NH- CH 2 -Ph

HCI salt: a white solid, mp 209-210 oC (EtOAc/MeOH), FT-IR (KBr) 3264 (m), 2922 (s), 2651 (m),
2783 (w), 2660 (m), 2496 (w), 1470 (w), 1424 (m), 1292 (w), 1158 (w), 1040 (w), 797 (w) cm-1 1H

NMR (CD 3 0D) 8 7.60-7.52 (m, 2H), 7.49-7.41 (m, 3H), 4.21 (s, 2H), 2.87 (d, J = 7.8 Hz, 2H),

1.84-1.62 (m, 6H), 1.40-1.15 (m, 3H), 1.06-0.96 (m, 2H); 13 C NMR (CD 3 0D) 8 132.5 (C), 131.2

(CH), 130.6 (CH), 130.2 (CH), 54.4 (CH 2 ), 52.7 (CH 2 ), 36.2 (CH), 31.6 (CH2), 27.0 (CH 2 ), 26.5

(CH2); El MS m/z (relative intensity) 203 ( M+, 2), 121 (7), 120 (74), 119 (5), 106 (6), 92 (10), 91
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(100), 65 (17), 55 (19). Analysis, calculated for C14H 2 2 NCI: C, 70.13; H, 9.25; N,
5.84; Cl,
14.79. Found: C, 69.82; H, 9.25; N, 5.96; Cl, 15.16.

N-(Cyclohexvlmethyl aniline: (Table II, entry 2 and Table V, entry 1)

NH-Ph

HCI salt, a white solid, mp 223-225 oC (EtOAc/MeOH). FT-IR (free base, neat): 3420 (m), 3052 (w),

2924 (s), 2850 (s), 1604 (s), 1507 (s), 1468 (w), 1449 (m), 1322 (m), 1257 (m), 1217 (w), 1179 (w),

1150 (w), 1113 (w), 866 (w), 748 (s), 692 (s), 628 (w), 561 (w), 508 (w) cm-1; 1H
NMR (free base,
CDC13 ): 5 7.14 (t, J = 6 Hz, 2H), 6.7 (m, 1H), 6.6 (d, J = 6 Hz, 2H), 3.9 (bs, 1H), 3.0 (d, J =
4 Hz,
2H), 2.0 (m, 6H), 1.3 (m, 3H), 1.1 (n,2H). 13C NMR (free base, CDCl 3 ): 8 148.6 (C), 129.2 (CH)
116.8 (CH), 112.6 (CH), 50.5 (CH2), 37.5 (CH), 31.3 (CH2), 26.6 (CH2), 26.0 (CH2); El MS m/z

(relative intensity) 189 (M+, 40), 1107 (26), 106 (100), 93 (5), 79 (13), 78 (6), 77 (30), 65 (6).
Analysis calculated for C13H20CIN: C, 69.16; H, 8.93; N, 6.20; Cl, 15.70. Found: C, 69.32; H, 9.05;

N, 5.98; Cl, 15.69.

4-(Cyclohexvlmethyl) morpholine: (Table II, entries 3 & 4)

NO0

HCI salt: a white solid, mp 249-250 oC (EtOAc/MeOH). FT-IR (KBr) 3424 (w), 2927 (vs), 2854 (s),
2611 (s), 2479 (s), 1443 (s), 1265 (m), 1120 (s), 906 (m) cm- 1 ; 1H NMR (CDCl ) 8 3.69 (t, J =
3 4.5
Hz, 4H), 2.46-2.30 (m, 4H), 2.11 (d, J = 7.2 Hz, 2H), 1.82-1.63 (m, 5H), 1.51-1.45 (m, 1H), 1.30-

1.12 (m, 3H), 0.93-0.80 (m, 2H); 13C

NMR (CDCl 3 ) 8 67.0 (CH 2 ), 66.1 (CH 2 ), 59.2 (CH2 ), 34.6

(CH), 31.8 (CH 2 ), 26.8 (CH 2 ), 26.1 (CH2 ); El MS n/z (relative intensity) 183 (11), 101 (15), 100

(100), 70 (10), 56 (23), 55 (18). Analysis calculated for C 1 lH 2 2 CINO: C, 60.12; H, 10.09; N, 6.37;
Cl, 16.13. Found: C, 60.33; H, 10.31; N, 6.51; Cl, 16.14.
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N-(Cyclohexvlmethyl) diethyl amine: (Table II, entry 5)

~ N

HCl salt: a white solid, mp 155-157 oC (EtOAc/MeOH). FT-IR (KBr) 3449 (s), 2929 (s), 2853 (m),
2793 (s), 2585 (w), 2364 (w), 1571 (w), 1430 (w), 749 (w), 749 (m), 606 (m) cm- 1; 1H NMR (CDCl )
3

8 10.90 (bs, 1H), 3.15 (bs, 4H), 2.81 (d, J = 6.7 Hz, 2H), 1.97 (bd, J = 12.2 Hz, 2H), 1.82-1.58 (m,
4H), 1.38 (t, J = 7.2 Hz, 6H), 1.34-0.94 (m, 5H); 13 C NMR (CDCl 3 ) 8 58.1 (CH2 ), 47.7 (CH 2 ), 33.4
(CH), 31.6 (CH 2 ), 25.7 (CH 2 ), 25.5 (CH2), 8.6 (CH 3 ); El MS m/z (relative intensity) 169 (3), 97 (8),
95 !00), 59 (19), 56 (9), 55 (14). Analysis calculated for C 11H24 CIN: C, 64.21; H, 11.76; N, 6.81;
Cl, 17.23. Found: C, 64.25; H, 11.72; N, 6.79; Cl, 17.48.

N-(Cyclohexylmethyl) diisopropvl amine: (Table 2, entries 6 & 7)

HCI salt: a white solid, mp 161-162 oC (EtOAc/MeOH). FT-IR (KBr) 3266 (s), 2991 (w), 2928 (s),
2853 (m), 2763 (w), 2650 (s), 2501 (w), 1451 (w), 1421 (w) cm- 1 ; 1H NMR (free base, CDCl 3 ) 8 2.96

(sept., J = 6.5 Hz, 2H), 2.17 (d, J = 7.0 Hz, 2H), 1.88-1.60 (m, 5H), 1.36-1.08 (m, 4H), 0.95 (d, J =
6.3 Hz, 12H), 0.80 (m, 2H); 13 C NMR (free base, CDCl 3 ) 8 51.7 (CH 2 ), 47.7 (CH), 37.4 (CH), 31.9
(CH 2 ), 27.2 (CH 2 ), 26.5 (CH 2 ), 20.8 (CH 3 ); El MS n/z (relative intensity) 197 (M+, 8), 182 (13), 115
(13), 114 (100), 72 (53), 56 (13), 55 (20). Analysis calculated for C13H 28 CIN: C, 66.78; H, 12.07; N,
5.99; Cl, 15.16. Found: C, 66.93; H, 12.31; N, 5.89; Cl, 15.09.

1-Hexyl-4-phenylpiperazine: (Table II, entry 8)

C6H1z-N N0

Oxalate salt: a white solid, mp 208-210 oC (decpn.) (MeOH). FT-IR (KBr) 3436 (m), 3027 (m), 2924

(s), 2854 (s), 2680 (m), 2590 (m), 1724 (s), 1637 (s), 1600 (vs), 1498 (s), 1456 (m), 1184 (s), 695
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(s), 478 (s) cm- 1; 1 H NMR (MeOH-d4) 8 7.28 (dd, Jj = 7.9, J2 = 7.3 Hz, 2H), 7.01 (d, J = 7.9 Hz,

2H), 6.92 (t, J = 7.3 Hz, 1H), 3.50-3.40 (m, 8 H), 3.20-3.15 (m, 2H), 1.85-1.70 (m, 2H), 1.45-1.30
(m, 6H), 0.93 (t, J = 6.8 Hz, 3H); 13 C NMR (MeOH-d4) 8 130.4 (CH), 122.4 (CH), 118.1 (CH), 58.2
(CH2), 53.2 (CH2), 48.2 (CH2), 32.4 (CH2), 27.4 (CH2), 25.1 (CH2), 23.5 (CH2), 14.3 (CH3); El

MS m/z (relative intensity) 246 (M+, 25), 175 (100), 160 (5), 147 (5), 132 (25), 105 (18), 104 (20), 91
(8), 87 (10), 77 (19)70 (53). Analysis calculated for: C1 8 H2 8 N 2 0 4 : C, 64.26; H, 8.39; N, 8.33.
Found: C, 64.27; H, 8.40; N, 8.20.

V-(3-Methoxvbenzvl) aniline: (Table II, entries 9 & 10 and Table V, entry 2)

CH 3 0
CH 2 -N-Ph
H

HCI salt, a white solid, mp 174-175 OC (EtOAc/MeOH). FT-IR (KBr) 3394(s), 3274(s), 2887(s),
2751(s), 2576(m), 2519(w), 2464(w), 1600(m), 1488(m), 1429(w), 1269(s), 1173(m), 1039(m),
799(w), 693(m) cm- 1 ; 1H NMR (DMSO-dd/D20) 8 7.56 (m, 3H), 7.37-7.33 (m, 3H), 7.02-6.94 (m,
2H), 6.96 (bs, 1H), 4.57 (s, 2H), 3.78 (s, 3H); 13 C NMR (DMSO-d6/D20) 5 158.9 (C), 134.7 (C),
132.1 (C), 130.1 (CH), 129.9 (CH), 128.9 (CH), 122.3 (CH), 122.2 (CH), 115.3 (CH), 114.8 (CH),

54.9 (CH 3 ), 53.9 (CH2 ); El MS m/z (relative intensity) 213 (M+, 43), 212 (13), 122 (9), 121 (100) 106
(21), 104 (9), 92 (7), 91 (27), 78 (21), 77 (37), 65 (23). Analysis calculated for C14 H 16 CIN: C, 67.33;
H, 6.46; N, 5.61; Cl, 14.20. Found: C, 67.38; H, 6.47; N, 5.51; Cl, 14.05.

4-(3-Methoxybenzyl)morpholine : (Table II, entry 11)

CH 30
CH2-N O

HCI salt: a white solid, mp 201-202 OC (EtOAc/MeOH). FT-IR (KBr) 3384 (s), 3273 (s), 2930 (m),
2652 (m), 2605 (m), 2475 (w), 1587 (m), 1460 (m), 1270 (s), 1161 (w), 1122 (w), 1086 (w), 1040
(m), 977 (w), 780 (m) cm- 1; 1 H NMR (free base, CDCl3 ) 8 7.30-7.21(m, 1H), 6.96-6.90 (m, 2H),
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6.85-6.76 (m, 1H), 3.80 (s, 3H), 3.76-3.66 (m, 4H), 3.46 (s, 2H), 2.50-2.38 (m, 4H); 13C NMR (free
base, CDCl 3 ) 8 159.6 (C), 139.4 (C), 129.1 (CH), 121.4 (CH), 114.6 (CH), 112.4 (CH), 67.0 (CH ),
2
63.3 (CH 2 ), 55.1 (CH 2 ), 53.6 (CH 3 ); CI MS m/z (relative intensity) 208 (MH+, 24), 207 (9), 206 (13),
149 (12), 139 (10), 138 (15), 122 (57), 121 (100), 109 (17), 100 (15), 91 (8), 86 (50). Analysis
calculated for C12Hl 8 CINO: C, 59.14; H, 7.44; N, 5.75; Cl, 14.55. Found: C, 59.27; H, 7.48; N,
5.59; Cl, 14.52.

N-tert-Butyl benzvl amine: (Table II, entry 12)

Ph- CH 2 -NH- t-Bu

HCI salt, a white solid, mp 246-247 OC (EtOAc/MeOH). FT-IR (KBr) 3438 (w), 2977 (s), 2941 (s),
2742 (vs), 2659 (m), 2627 (m), 2589 (m), 2427 (w), 1580 (m), 1452 (m), 1401 (w), 1375 (m), 1240

(w), 1190 (w), 987 (w), 706 (m), 697 (s), 507 (m) cm- 1; 1H NMR (DMSO-d 6 ) 8 9.45 (bs, 2H), 7.71-
7.68 (m, 2H), 7.42-7.35 (m, 3H), 4.07 (bs, 2H), 1.42 (s, 9H); 13 C NMR (DMSO-d 6 ) 8 132.7 (C),
130.4 (CH), 128.6 (CH), 128.4 (CH), 56.8 (C), 44.5 (CH2 ), 25.1 (CH 3 ); CI MS m/z (relative
intensity): 164 (MH+, 4), 162 (7), 149 (11), 148 (100), 108 (17), 106 (5), 91 (99). Analysis calculated
for C11 H17 CIN: C, 66.15; H, 9.08; N, 7.01; Cl, 17.75. Found: C, 65.99; H, 8.83; N, 6.77; Cl, 17.74.

exo-N-Benzyl-2-aminonorbomane: (Table II, entry 14)

H
N Ph
H

HCI salt: a white solid, mp >265 oC (EtOAc/MeOH). FT-IR (KBr) 3400 (m), 2968 (s), 2926 (s), 2811
(m), 2762 (m), 1459 (m), 1424 (s), 745 (m), 692 (s), 504 (m) cm -1; 1 H NMR (CDCl3) 8 9.70 (bs,

2H), 7.64 (dd, Jj = 7.8, J2 = 1.3 Hz, 2H), 7.46-7.32 (m, 3H), 4.10 & 3.95 (AB q, J = 13.6 Hz, 2H),

2.82-2.69 (m, 2H), 2.40 (bs, 1H), 2.22 (d, J = 10.7 Hz, 1H), 1.87-1.70 (m, 1H), 1.65-1.40 (m, 3H),
1.30 (d, J = 10.1 Hz, IH), 1.10-0.94 (m, 2H); 13 C NMR (DMSO-d 6 ) 8 133.7 (C), 132.2 (CH), 130.5

(CH), 130.2 (CH), 61.6 (CH), 49.9 (CH 2 ), 40.3 (CH), 37.3 (CH), 37.25 (CH 2 ), 36.3 (CH2 ), 29.1,
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(CH 2 ), 28.4 (CH 2 ); El MS m/z (relative intensity) 201 (M+, 10), 172 (10), 132 (17), 110 (25), 91

(100), 77 (5), 65 (22). Analysis calculated for C14 H2 0 CIN: C, 70.72; H, 8.48; N, 5.89; Cl, 14.91.
Found: C, 70.69; H, 8.55; N, 5.89; Cl, 15.00.

N-Benzvl-1-aminoadamantane: (Table II, entry 15)

HN--
6PPh

HC salt, a white crystalline solid, mp >265 'C (EtOAc/MeOH). FT-IR (KBr) 3449 (w), 2918 (s), 2853

(m), 2825 (m), 2761 (m), 2417 (w), 1454 (m), 1376 (w), 1071 (w), 694 (m) cm- 1; 1H NMR (DMSO-

d6) 8 9.22 (bs, 2H), 7.70-7.60 (m, 2H), 7.50-7.35 (m, 3H), 4.15-4.05 (m, 2H), 2.20-2.10 (m, 3H),

2.05-2.00 (m, 6H), 1.80-1.55 (m, 6H); 13 C

NMR (CDCl3/DMSO-d 6 ) 8 131.7 (CH), 130.4 (C), 128.5
(CH), 128.3 (CH), 57.4 (C), 42.9 (CH2), 37.6 (CH2), 35.2 (CH2), 28.6 (CH); El MS m/z (relative

intensity) 241 (M+, 18), 85 (9), 184 (45), 147 (8), 135 (9), 105 (22), 91 (100), 79 (11), 77 (12).
Analysis, calculated for Cl7H24 CIN: C, 73.49; H, 8.71; N, 5.04; Cl, 12.76. Found: C, 73.10; H, 8.66;
N, 5.36; Cl, 12.91.

N-r(1-methvl pyrrol-2-vl) methyll hexamethylene imine: (Table I, entry 16)

CH3

Free base: a colorless oil. Oxalate salt: a reddish brown solid, mp 148-149 oC (EtOAc/MeOH). FT-IR
(KBr) 3425 (w), 2938 (s), 2621 (s), 1719 (m), 1631 (s), 1460 (m), 1402 (s), 1207 (s), 1099 (m), 723

(vs) cm- 1; 1H NMR (free base, CDC1) 3 8 6.54 (d, J = 2.0 Hz, 1H), 6.00 (d, J = 2.9 Hz, 1H), 5.94 (bs,
1H), 3.65 (s, 3H), 3.49 (s, 2H), 2.55 (bs, 4H), 1.57 (bs, 8H); 13C
NMR (free base, CDCl 3 ) 8 130.6
(C), 122.2 (CH), 108.7 (CH), 105.9 (CH), 54.8 (CH2 ), 54.4 (CH 2 ), 33.8 (CH 3 ), 28.4 (CH ), 27.0
2
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(CH2); El MS m/z (relative intensity) 192 (M+, 6), 98 (10), 95 (12), 94 (100), 78 (2), 67 (3). Analysis
calculated for C 14H 22 N2 0 4 : C, 59.56; H, 7.85; N, 9.92. Found: C, 59.61; H, 7.66; N, 9.88.

Ethyl 1-(3-nitrobenzyl)piperidine-2-carboxylate: (Table II, entry 18)

NO 2 CO 2Et

Free base: a pale yellow oil. FT-IR (neat) 2939 (s), 2858 (m), 1732 (s), 1530 (s), 1445 (w), 1350 (s),
1264 (w), 1183 (s), 1026 (w) 808 (w), 732 (m) cm- 1; 1 H NMR (CDCl 3 ) 8 8.22 (s, 1H), 8.10 (d, J =
8.1 Hz, 1H), 7.73 (d, J = 7.6 Hz, 1H), 7.49 (dd, Jj = 8.1, J2 = 7.6 Hz, 1H), 4.23 (q, J = 7.1 Hz, 2H),
3.90 (d, J = 14.0 Hz, 1H), 3.52 (d, J = 14.0 Hz, 1H), 3.24-3.20 (m, 1H), 2.96-2.88 (m, 1H), 2.25-

2.18 (m, 1H), 1.90-1.80 (m, 2H), 1.70-0.80 (m, 4H), 1.31 (t, J = 7.1 Hz, 3H); 13 C NMR (CDCl3) 8
173.2 (C), 148.0 (C), 141.0 (C),134.7 (CH), 128.8 (CH), 123.2 (CH), 121.7 (CH), 63.7 (CH), 60.4
(CH2), 60.0 (CH2), 49.6 (CH2), 29.2 (CH2), 25.0 (CH2), 21.9 (CH2), 14.0 (CH3); El MS m/z

(relative intensity) 219 (M+-CO 2 Et, 100), 173 (10), 136 (19), 90 (16), 55 (7). Analysis calculated for
C 1 5 H 20 N2 0 4 : C, 61.63; H, 6.90; N, 9.58. Found: C, 61.53; H, 6.86; N, 9.49.

NVN Diethyl-48,13,17.21 -pentamethyl-4.8,12,16, 2 0-docosapentaenylamine (allE) (Squalene

diethylamine): 29 (Table II, entry 19)

KI

Crude free base: a pale pink oil. FT-IR (neat) 2968 (s), 2926 (vs), 2853 (s)1667 (w), 1447 (m), 1381
(m), 1202 (w), 1087 (w), 837 (w) cm- 1 ; 1H NMR (CDCl 3 ) 8 5.11-4.98 (m, 5H), 2.48 (q, J = 7.1 Hz,

4H), 2.38-2.29 (m, 2H), 2.08-1.85 (m, 18 H), 1.60 (s, 18 H), 1.53-1.49 (m, 2H), 0.99 (d, J = 6.6
Hz, 12 H); 13 C NMR (CDCl 3 ) 8 ; 134.91 (C), 134.87 (C), 134.71 (C), 134.4 (C), 131.1 (C), 124.28

(CH), 124.25 (CH), 124.16 (CH), 124.14 (CH), 124.11 (CH), 52.3 (CH2), 46.7 (CH ), 39.6 (CH ),
2 2
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37.4 (CH2 ), 28.1 (CH 2 ), 26.6 (CH2), 26.5 (CH2 ), 25.5 (CH ), 24.8 (CH ), 17.5 (CH
2 2 3 ), 15.9 (CH 3 ),
15.8 (CH3 ), 15.7 (CH3 ), 11.4 (CH 3 ). El MS m/z (relative intensity) 441 (M+, 12), 426 (6), 372 (14),

304 (17), 236 (6), 168 (20), 112 (7), 99 (20), 86 (100), 72 (9), 69 (26). Accurate mass calculated for

C3 1H56 N+ (MH+): 442.4413. Found: 442.4424± 0.0027, difference: 2.5 ppm.

N.N. Di(2-proplyl-4.8.13.17.21-pentamethyl-4.8.12.16.20-docosapentaenylamine (all E) (Squalene

diisompylamine):29 (Table II, entry 20)

Free base: a pale yellow oil. FT-IR (neat) 3691 (w), 2968 (s), 2927 (s), 1664 (w), 1602 (w), 1447 (m),

1384 (m), 1227 (s), 1133 (w), 983 (w), 841 (w), 800 (s) cm- 1; 1H NMR (CDCl ) 8 5.14-5.07 (m, 5H),
3

3.00 (septet, J = 6.5 Hz, 2H), 2.40-2.30 (m, 2H), 2.20-1.90 (m, 18 H), 1.60 (s, 18 H), 1.53-1.49 (m,

2H), 0.99 (d, J = 6.6 Hz, 12 H); 13 C NMR (CDCl 3 ) 8 134.9 (C), 134.7 (C), 131.0 (C), 124.3 (CH),
124.2 (CH), 124.1 (CH), 124.0 (CH), 48.8 (CH), 45.1 (CH 2 ), 39.60 (CH ), 39.58 (CH ), 37.3
2 2
(CH 2 ), 29.2 (CH2 ), 26.6 (CH 2 ), 26.5 (CH2 ), 25.5 (CH ), 21.6 (CH ), 20.3 (CH ),
2 3 3 17.5 (CH 3 ), 15.9
(CH3 ), 15.8 (CH3 ); El MS m/z (relative intensity) 469 (M+, 7), 455 (16), 454 (44), 332 (12), 264 (5),

196 (23), 127 (19), 114 (100), 72 (14), 69 (28). Accurate mass calculated for C3 H 0N* (MH+):
3 6
470.4726. Found: 470.4733+ 0.0017, difference: 1.5 ppm.

1.5-bis(4-Phenvlpiperazin-1-yl)pentane: (Table II, entry 21)

Ph-N N-(CH2) 5 -N N-Ph

Dioxalate salt mp 218-220 oC (decpn.) (MeOH). FT-IR (KBr) 3469 (s), 3000 (w), 2920 (s), 2837 (m),

2679 (s), 2601 (s), 1719 (s), 1596 (s), 1499 (s), 1402 (s), 1279 (s), 1225 (s), 1101 (s), 770 (m), 722
(s), 502 (s) cm- 1 ; 1IH NMR (free base, CDCl3) 8 7.25 (dd, J1 = 7.9, J2 = 7.3 Hz, 4H), 6.93 (d, J = 7.9

Hz, 4H), 6.85 (t, J = 7.3 Hz, 2H), 3.21 (t, J = 4.9 Hz, 8H), 2.60 (t, J = 4.9, 8H), 2.40 (t, J = 7.7 Hz,
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4H), 1.62-1.52 (m, 4H), 1.37 (quintet, J = 7.2 Hz, 2H); 13C
NMR (free base, CDCl3) 8 151.2 (C),
129.0 (CH), 119.5 (CH), 115.9 (CH), 58.6 (CH2), 53.2 (CH2), 49.0 (CH2), 26.7 (CH2), 25.5
(CH2); ESI-MS m/z 393 (MH+), 197. Analysis calculated for: C29 H4 0 N4 0 8 : C, 60.82; H, 7.04; N,

9.78. Found: C, 60.57; H, 7.02; N, 9.53.

1-Methyl-4-p2henvlpiperazine: (Table II, entry 22)

/ -1
H 3 C-N N-Ph

Oxalate salt: a white crystalline solid, mp 152-154 'C (MeOH). FT-IR (KBr) 3436 (w), 3027 (m), 2924

(s), 2854 (m), 2680 (m), 2590 (m), 1724 (s), 1637 (s), 1600 (s), 1498 (s), 1238 (s), 1183 (s), 695 (m),

478 (s) cm-1; 1H NMR (DMSO-d 6 ) 8 12.00 (bs, 1H), 7.25 (dd, J1 = 7.2, J2 = 8.1 Hz, 2H), 6.97 (d, J
= 8.1 Hz, 2H), 6.85 (t, J = 7.2 Hz, 1H), 3.50-3.20 (m, 8H), 2.78 (s, 3H); 13C
NMR (DMSO d6) 5
166.8 (C), 151.4 (C), 130.8 (CH), 121.6 (CH), 117.6 (CH), 53.9 (CH2), 47.3 (CH2), 44.0 (CH3); El

MS n/z (relative intensity) 176 (M+, 56), 161 (6), 132 (13), 106 (16), 105 (50), 104 (29), 77 (31),71
(40), 70 (30). Analysis calculated for: C13 Hl 8N 2 0 4 : C, 58.63; H, 6.81; N, 10.52. Found: C, 58.50;
H, 6.74; N, 10.50.

N-Cyclopentvl-4-bromoaniline: (Table m, entry 1)

Br H
HCI salt: a white solid, mp 210-212 oC (EtOAc/MeOH). FT-IR (KBr) 2963 (m), 2899 (s), 2790 (s),

2723 (s), 2650 (s), 2532 (s), 2456 (s), 1572 (m), 1487 (s), 1446 (m),1336 (m), 1073 (m), 1015 (m),

834 (m), 777 (m), 566 (m), 509 (s), 459 (m) cm -1; 1H NMR (free base, CDCl3) 8 7.21 (d, J = 8.8 Hz,

2H), 6.44 (d, J = 8.8 Hz, 2H), 3.80-3.50 (quintet and bs, J = 6.1 Hz, 2H), 2.10-1.90 (m, 2H), 1.80-

1.60 (m, 4H), 1.50-1.30 (m, 2H); 13 C

NMR (free base, CDCl3) 8 146.9 (C), 131.7 (CH), 114.6 (CH),

108.2 (C), 54.5 (CH), 33.3 (CH2), 23.9 (CH2); El MS n/z (relative intensity) 241 (56), 240 (13), 239

(56),213 (10), 212 (75), 211 (12), 210 (74), 199 (38), 197 (39), 173 (16), 171 (19), 157 (10), 155

(10), 132 (15), 131 (35), 130 (100), 118 (16), 117 (35), 92 (26), 91 (36), 90 (13), 77 (14), 76 (21), 75
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(19). Analysis calculated for: C11HI5BrCIN: C, 47.77; H, 5.47; N, 5.06; Br, 28.89; Cl, 12.82. Found:
C, 47.39; H, 5.35; N, 4.96; Br, 29.00; Cl, 12.86.

N-Cyclohexyl-4-nitroaniline: (Table III, entry 2)

Na NO02

Free base: yellow crystals, mp 97-99 oC (EtOAc/hexane). FT-IR (KBr) 3344 (s), 2933 (m), 2855 (w),
1600 (vs), 1540 (m), 1486 (m), 1296 (vs), 1256 (m), 1181 (w), 1111(s), 833 (m), 754 (w) cm- 1; 1 H

NMR (CDC1) 3 8 8.06 (d, J = 9.1 Hz, 2H), 6.50 (d, J = 9.1 Hz, 2H), 4.54-4.48 (m, 1H), 3.40-3.30

(m, 1H), 2.05 (d, J = 10.0 Hz, 2H), 1.88-1.74 (m, 2H), 1.74-1.62 (m, 1H), 1.50-1.35 (m, 2H), 1.35-
1.18 (m, 3H); 13 C NMR (CDCl 3 ) 8 152.5 (C), 137.3 (C), 126.5 (CH), 111.1 (CH), 51.5 (CH), 32.8

(CH 2 ), 25.5 (CH 2 ), 24.7 (CH2 ); CI MS m/z (relative intensity) 221 (MH*, 100), 220 (42), 205 (11),
204 (27), 177 (36), 167 (9), 164 (4), 150 (4), 139 (6). Analysis calculated for C12 H 16 N2 0 2 : C, 65.43;
H, 7.32; N, 12.72. Found: C, 65.29; H, 7.38; N, 12.75.

N-Cyclohexyl-4-chloroaniline: (Table m, entry 3)

HCI salt: white crystals, mp 210-212 OC (EtOAc/MeOH). FT-IR (KBr) 3400 (m), 2940 (s), 2859 (m),
2778 (m), 2743 (m), 2679 (m), 2641 (m), 2596 (m), 2490 (s), 2428 (m), 1492 (s), 1456 (m), 1006
(m), 1016 (m), 841 (w), 560 (m), 507 (m) cm-1; 1H NMR (DMSO-d 6 ) 8 11.15 (bs, 1H), 7.60-7.49 (m,

5H), 3.40-3.31 (m, 1H), 1.92 (d, J = 10.7 Hz, 2H), 1.74 (d, J = 13.1 Hz, 2H), 1.58 (d, J = 12.2 Hz,

1H) 1.51-1.40 (m, 2H), 1.30-1.17 (m, 2H), 1.11 (t, J = 12.3 Hz, 1H); 13H NMR (DMSO-d 6 ) 8 134.6
(C), 129.6 (CH), 125.0 (CH), 59.4 (CH), 28.8 (CH 2 ), 24.8 (CH 2 ), 24.0 (CH 2 ); CI-MS m/z (relative

intensity) 212 (MH*, 30), 211 (45), 210 (91), 209 (100), 175 (12), 174 (67), 168 (9), 166 (23), 130
(10), 128 (19), 83 (15). Analysis calculated for C12HI 7Cl 2 N: C, 58.55; H, 6.96; N, 5.69; Cl, 28.80.

Found: C, 58.35; H, 6.89; N, 5.53; Cl, 29.01.

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4 -(4-Chiorophenyl amino)-1-carbethoxy piperidine: (Table III, entry 4)

EtOOC- ND H-O Cl

Free base: white crystals, mp 121-123 oC (Et2O/hexane). FT-IR (KBr) 3327 (s), 2995 (w), 2940 (m),

2876 (w), 1673 (vs), 1599 (s), 1524 (m), 1485 (s), 1339 (s), 1373 (w), 1310 (m), 1231 (s), 1154 (m),
1080 (m), 1020 (w), 819 (m), 770 (m) cm- 1; 1H NMR (CDCl3) 8 7.09 (d, J = 8.6 Hz, 2H), 6.50 (d, J

= 8.6 Hz, 2H), 4.18 - 4.10 (m, 4H), 3.63 (bs, 1H), 3.38 (bs, 1H), 2.95 (t, J = 12.0 Hz, 2H), 2.01 (d,
J = 11.0 Hz, 2H), 1.36-1.22 (m, 2H), 1.26 (t, J = 7.0 Hz, 3H); 13 C NMR (CDC13 ) 5 155.4 (C), 145.3
(C), 129.1 (CH), 121.8 (C), 114.3 (CH), 61.3 (CH 2 ), 50.0 (CH), 42.6 (CH 2 ), 32.1 (CH 2 ), 14.7

(CH 3 ); El MS m/z (relative intensity) 284 (M+, 21), 283 (10), 282 (M+, 65), 255 (2), 253 (7), 211(7),
209 (23), 168 (10), 167 (16), 165 (35), 156 (81), 154 (20), 153 (23), 152 (22), 132 (20), 131 (86), 129
(17), 128 (24), 127 (80), 126 (62), 118 (15), 117 (23), 111 (22), 101 (13), 100 (26), 91 (23), 84 (26),
83 (22), 82 (47), 68 (39), 56 (100), 55 (47). Analysis calculated for C14H19N2C02 : C, 59.47; H,

6.77; N, 9.91; Cl, 12.54. Found: C, 59.62; H, 7.10; N, 9.86; Cl, 13.50

N-Cycloheptyl p-anino benzoic acid: (Table III, entry 6)

H-- COOH

White solid, mp 159-160 oC (Et2O/hexane). FT-IR (KBr) 3413 (m), 2927 (s), 2665 (m), 2596 (w),
2542 (m), 1665 (s), 1608 (s), 1524 (m), 1416 (s), 1342 (m), 1316 (m), 1284 (s), 1175 (s), 1124 (m),
945 (m), 839 (m), 775 (m), 644 (m) cm- 1 ; 1H NMR (DMSO-d6 ) 8 11.95 (s, 1H), 7.68 (d, J = 8.6 Hz,

2H), 6.52 (d, J = 8.6 Hz, 2H), 6.29 (d, J = 7.4 Hz, IH), 3.45 (bs, 1H), 1.94-1.82 (m, 2H), 1.71-1.39
(m, 10H); 13 C NMR (DMSO-d 6 ) 8 167.6 (C), 151.5 (C), 131.2 (CH), 116.3 (C), 111.1 (CH), 52.3

(CH), 33.8 (CH 2 ), 28.0 (CH2 ), 23.8 (CH 2 ); El MS n/z (relative intensity): 233 (M+, 37), 204 (4), 190
(22), 177 (15), 176 (100), 163 (14), 150 (15), 137 (13), 132 (14), 130 (14), 118 (14), 117 (10), 91 (7).

Analysis calculated for C14HI 9 N0 2 : C, 72.07; H, 8.21; N, 6.00. Found: C, 72.26; H, 8.12; N, 5.98.
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p-Cvano-N-cycloheptyl aniline: (Table III, entry 7)

HCEN

Free base: a white solid, mp 89-91 0 C (purified by column chromatography on silica gel using 10% Et 2 O
in hexane as eluent). FT-IR (KBr) 3343 (in), 2928 (m), 2853 (w), 2210 (m), 1607 (s), 1528 (s), 1459

(w), 1347 (s), 1171 (s), 1060 (w), 824 (s), 545 (in) cm- 1; 1H NMR (CDCl 3 ) 8 7.38 (d, J = 8.6 Hz,

2H), 6.48 (d, J = 8.6 Hz, 2H), 4.31 (bd, J = 6.0 Hz, 1H), 3.51-3.40 (in, 1H), 2.05-1.90 (in, 2H),
1.78-1.42 (m, 10H); 13 C NMR (CDCl 3 ) 8 150.4 (C), 133.7 (CH), 120.8 (C), 112.4 (CH), 97.6 (C),
53.3 (CH), 34.5 (CH2), 28.2 (CH 2 ), 24.2 (CH 2 ); El MS m/z (relative intensity): 214 (M+, 26), 185
(4), 171 (18), 158 (15), 157 (100), 144 (13), 131 (14), 118 (15), 102 (10). Analysis calculated for

C14HI 8 N 2 : C, 78.46; H, 8.47; N, 13.07. Found: C, 78.38; H, 8.38; N, 12.82.

Ethyl N-(2-heptyl)-4-aminobenzoate: (Table M, entry 8)

CH3H COOCH 2 CH 3

Free base: a colorless oil (purified by column chromatography on silica gel using 5% EtOAc in hexane as
eluent). FT-IR (CHCl3 ): 3427 (in), 2962 (s), 2932 (s), 2859 (m), 1696 (s), 1606 (s), 1524 (m), 1462
(w), 1368 (m), 1339 (in), 1283 (s), 1175 (in), 1109 (s), 1021 (w) cm- 1 ; 1H NMR (CDCl 3 ) 8 7.85 (d, J

= 8.7 Hz, 2H), 6.51 (d, J = 8.7 Hz, 2H), 4.30 (q, J = 7.2 Hz, 2H), 4.05 (bd, J = 6.9 Hz, 1H), 3.57-
3.45 (in, 1H), 1.50-1.23 (in, 8H), 1.35 (t, J = 7.2 Hz, 3H), 1.17 (d, J = 6.6 Hz, 3H), 0.88 (t, J = 6.7
Hz, 3H); 13 C NMR (CDCl 3 ) 8 167.0 (C), 151.5 (C), 131.5 (CH), 111.5 (CH), 60.1 (CH2), 48.2

(CH), 37.0 (CH 2 ), 31.8 (CH 2 ), 25.9 (CH 2 ), 22.6 (CH 2 ), 20.6 (CH 3 ), 14.5 (CH3 ), 14.0 (CH 3 ); El MS
m/z (relative intensity): 263 (M+, 11), 248 (6), 218 (7), 193 (13), 192 (100), 164 (25), 120 (12), 119
(14), 118 (9), 91 (7). Analysis calculated for C 16 H 2 5 NO 2 : C, 72.95; H, 9.57; N, 5.32. Found: C,

72.64; H, 9.39; N, 5.22.

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31

N-Cyclohexyl-2.4-dichloroaniline: (Table III, entry 9)

Cl

H Cl

Free base: a pale tan oil obtained by column chromatography on silics gel using 5% Et 2 O in hexane as
eluent. FT-IR (neat) 3416 (m), 2932 (s), 2856 (m), 1597 (s), 1505 (vs), 1449 (m), 1321 (m), 1266

(m), 1157 (m), 1109 (m), 866 (m), 801 (m), 749 (m) cm- 1; 1H NMR (CDC13 ) 8 7.22 (d, J = 2.4 Hz,

1H), 7.05 (dd, J1 = 8.8, J2 = 2.4 Hz, 2H), 6.56 (d, J = 8.8 Hz, 1H), 4.17 (bs, 1H), 3.34-3.11 (m,
1H), 2.08-1.95 (m, 2H), 1.83-1.79 (m, 2H), 1.79-1.58 (m, 1H), 1.47-1.12 (m, 5H); 1 3C NMR
(CDCl 3 ) 8 141.8 (C), 128.7 (CH), 127.5 (CH), 120.2 (C), 119.0 (C), 51.4 (CH), 32.9 (CH 2 ), 25.7

(CH 2 ), 24.7 (CH2 ); El MS m/z (relative intensity): 245 (M+, 31), 243 (M+, 52), 202 (65), 200 (100),
189 (10), 187 (17), 174 (15), 166 (15), 165 (21), 164 (35), 163 (22), 161 (35), 125 (11), 117 (15), 75
(11). Accurate mass calculated for C 1 2 Hl 6 NCl 2 + (MH+): 244.0660. Found: 244.0661+ 0.0038,

difference: 0.4 ppm.

N-(Cyclohexvlmethyl)-4-nitroaniline: (Table III, entryl3)

H-0 NO2

Yellow crystalline solid, mp 101-102 oC (Et20/hexane). FT-IR (KBr) 3345 (s), 2914 (s), 2848 (m),
1602 (s), 1543 (m), 1471 (m), 1284 (vs), 1180 (s), 1106 (s) cm-1; 1 H NMR (CDC1) 3 8 8.06 (d, J = 9.2

Hz, 2H), 6.50 (d, J = 9.2 Hz, 2H), 4.67 (bs, 1H), 3.05 (t, J = 5.8 Hz, 2H), 1.83-1.52 (m, 6H), 1.34-
1.10 (m, 3H), 1.08-0.90 (m, 2H); 13 C NMR (CDCl 3 ) 8 153.6 (C), 137.4 (C), 126.3 (CH), 110.8
(CH), 49.8 (CH 2 ), 37.4 (CH), 31.0 (CH 2 ), 26.2 (CH2 ), 25.7 (CH 2 ); EI-MS m/z (relative intensity):
234 (M+, 23), 151 (100), 135 (5), 105 (28), 76 (5). Accurate mass calculated for C1 3H N O2+
19 2
(MH+): 235.1447. Found: 235.1452+ 0.0032, difference: 2.1 ppm.
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N-(Cyclohexylmethyl)-4-aminobenzoic acid: (Table III, entry 14)

COOH

White solid, mp 182-184 oC (Et20/hexane). FT-IR (KBr) 3414 (m), 2930 (m), 2950 (w), 2666 (w),
2546 (w), 1666 (s), 1602(s), 1531 (w), 1485 (w), 1422 (m), 1317 (m), 1291 (s), 1177 (s), 1125 (w),

776 (w), 649 (w) cm- 1 ; 1H NMR (DMSO-d 6 ) 8 11.95 (s, 1H), 7.67 (d, J = 8.6 Hz, 2H), 6.56 (d, J =

8.6 Hz, 2H), 6.45 (t, J = 5.3 Hz, 1H), 2.90 (t, J = 6.0 Hz, 2H), 1.78 (d, J = 12.5 Hz, 2H), 1.72-1.49
(m, 4H), 1.29-1.09 (m, 3H), 1.01-0.88 (m, 2H); 13 C NMR (DMSO-d 6 ) 8 167.6 (C), 152.9 (C), 131.1
(CH), 116.4 (C), 110.5 (CH), 48.9 (CH 2 ), 36.8 (CH), 30.7 (CH2 ), 26.1 (CH 2 ), 25.5 (CH2 ); El MS
m/z (relative intensity): 233 (M+, 15), 151 (11), 150 (100), 105 (3), 79 (3), 77 (4), 65 (5). Analysis
calculated for C14 H 19 N0 2 : C, 72.07; H, 8.21; N, 6.00. Found: C, 71.78; H, 8.12; N, 5.96.

N-(Cyclohexylmethyl)-2.4-dichloroaniline: (Table III, entry 15)

Cl
H C
~~z7~-N-t } Cl

Free amine: a colorless oil (purified by flash column chromatography on silica gel using 5% Et2 O in
hexane as eluent). FT-IR (CHCl 3 ) 3432 (w), 2928 (s), 2853 (m), 1596 (m), 1506 (s), 1449 (w), 1325
(w), 1270 (w) cm- 1; 1H NMR (CDCl 3 ) 8 7.20 (d, J = 2.0 Hz, 1H), 7.04 (dd, J1 = 8.8, J2 = 2.0 Hz,

2H), 6.49 (d, J = 8.8 Hz, 1H), 4.30 (bs, 1H), 2.92 (t, J = 5.8 Hz, 2H), 1.88-1.62 (m, 5H), 1.62-1.50
(m, 1H), 1.33-1.10 (m, 3H), 1.05-0.91 (m, 2H); 13 C NMR (CDCl 3 ) 8 143.0 (C), 128.5 (CH), 127.6
(CH), 120.4 (C), 119.1 (C), 111.5 (CH), 50.3 (CH 2 ), 37.3 (CH), 31.2 (CH 2 ), 26.5 (CH 2 ), 25.9
(CH2); El MS m/z (relative intensity): 259 (M+, 10), 258 (3), 257 (M+, 16), 178 (11), 177 (7), 176
(87), 175 (13), 174 (100), 139 (4), 111 (9). Analysis calculated for C13H 17 Cl 2 N: C, 60.48; H, 6.64;
N, 5.42; Cl, 27.46. Found: C, 60.59; H, 6.80; N, 5.28; Cl, 27.16.
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N-(Cyclohexvlmethyl)-o-nitroaniline: (Table In, entry 16)

NO 2

Free base: a yellow oil (purified by flash column chromatography on silica gel using
5% Et2 0 in hexane
as eluent). FT-IR (CHCl 3 ) 3387 (m), 2929 (s), 2854 (m), 1620 (s), 1580 (s), 1513 (s),
1467 (w), 1418
(w), 1354 (m), 1267 (s), 1158 (m), 1038 (w) cm- 1; IH NMR (CDCl ) 8 8.13 (d,
3 J = 8.9 Hz, 2H), 7.40
(t, J = 7.8 Hz, 1H), 6.82 (d, J = 8.8 Hz, 1H), 6.59 (t, J = 7.8 Hz, 1H), 3.13 (t, J = 6.0
Hz, 2H), 1.90-
1.60 (m, 6H), 1.37-1.11 (m, 3H), 1.10-0.99 (m, 2H); 13
C NMR (CDC13 ) 8 136.1 (C), 126.8 (C),
114.8 (CH), 113.8 (CH), 49.5 (CH 2 ), 37.3 (CH), 31.1 (CH ), 26.3 (CH ), 25.8
2 2 (CH 2 ); El MS m/z
(relative intensity): 234 (M+, 14), 188 (3), 152 (11), 151 (100), 135 (9), 134 (9), 105
(11), 104 (9), 93
(17), 78 (12), 77 (12). Analysis calculated for C13HI N 0 : C, 66.64; H, 7.74;
8 2 2 N, 11.96. Found: C,
66.64; H, 7.78; N, 12.09.

N-3-Phonylpropy-2.4-dichloroaniline: (Table III, entry 17)

H C
PhN

Cl

HCI salt: white crystals, mp 143-145 oC (EtOAc/hexane). FT-IR (KBr) 3062 (w), 3026 (w), 2918 (s),
2877 (m), 2624 (s), 2570 (s), 2464 (s), 2387 (s), 2070 (w), 1567 (s), 1492
(vs), 1450 (m), 1406 (w),
1107 (w), 859 (m), 700 (m) cm- 1 ; 1H NMR (CDC13 ) 8 10.30 (bs, 1H), 7.89 (d,
J = 8.6 Hz, 1H), 7.42
(d, J = 2.2 Hz, 1H), 7.28-7.10 (m, 6H), 3.39-3.30 (m, 2H), 2.66 (t, J = 7.6
Hz, 2H), 2.33-2.20 (m,
13
2H); C NMR (CDCl 3 ) 8 139.4 (C), 136.0 (C), 131.4 (C), 130.8 (CH), 129.2
(C), 128.42 (CH),
128.38 (CH), 128.13 (CH), 126.8 (CH), 126.3 (CH), 51.0 (CH ), 32.4 (CH
2 2 ), 26.8 (CH 2 ); El MS
m/z (relative intensity): 281 (M+, 20), 279 (30), 244 (2), 187 (6), 177 (6), 176
(67), 175 (11) 174
(100), 163 (20), 161 (31), 133 (7), 117 (12), 111 (15), 91 (47), 78 (7), 77 (14). Analysis
calculated for
Cl5HI6Cl 3 N: C, 56.90; H, 5.09; N, 4.42; Cl, 33.59. Found: C, 56.90; H, 4.96; N, 4.46; Cl, 33.61.
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N-Benzyl-4-nitroaniline: (Table III, entryl8)

CH 2 - N NO 2

Free base: yellow crystals, mp 146-148 oC (EtOAc/hexane). FT-IR (KBr) 3367 (s), 1603 (s), 1541 (m),
1473 (m), 1279 (s), 1182 (m), 1106 (s), 998 (w), 932 (m), 733 (m) cm- 1; 1 H NMR (CDCl ) 8 8.08 (d,
3

J = 8.9 Hz, 2H), 7.40-7.30 (m, 5H), 6.57 (d, J = 8.9 Hz, 2H), 4.92 (bs, 1H), 4.44 (d, J = 5.3 Hz,
2H); 13C NMR (CDCl 3 ) 8 153.0 (C), 138.3 (C), 137.3 (C), 129.0 (CH), 127.9 (CH), 127.4 (CH),

126.4 (CH), 111.3 (CH), 47.6 (CH 2 ); CI MS m/z (relative intensity): 229 (MH+, 100), 213 (12), 212
(19), 191 (32),183 (4), 151 (8), 83 (4). Analysis calculated for C 13H12 N2 0 : C, 68.41; H, 5.30; N,
2
12.27. Found: C, 68.32; H, 5.33; N, 12.29.

N-( 4 -Chloro- 3 -trifluromethylphenyl)-4-nitrpbenzylamine: (Table III, entry 19)

CF 3
02N-Q- CH-j- Cl

Free amine: orange crystals, mp 103-104 oC (ether/hexane). FI-IR (KBr) 3423 (s), 1613 (m), 1519 (s),
1300? (vs), 1114 (s) cm-1 1H NMR (CDCl 3 ) 8 8.18 (d, J = 8.7 Hz, 2H), 7.51 (d, J = 8.7 Hz, 2H),

7.22 (d, J = 8.7 Hz, 1H), 6.885 (d, J = 2.85 Hz, 1H), 6.61 (dd, Jj = 2.85 Hz, J2 = 8.7 Hz, 1H), 4.45-
4.48 (m, 3H); 13 C NMR (CDCl 3 ) 8 147.3 (C), 145.9 (C), 145.7 (C), 132.1 (CH), 128.7 (q, J = 52.8

Hz, C), 127.6 (CH), 123.9 (CH), 122.69 (q, J = 243 Hz, CF 3 ), 119.8 (C), 116.1 (CH), 111.62 (q, J =
5.6 Hz, C), 47.3 (CH 2 ); El MS n/z (relative intensity): 332 (34), 331 (100), 329 (10), 311 (5), 284
(7), 283 (7), 210 (8), 208 (26), 206 (6), 179 (10), 136 (59), 107 (10), 106 (43), 90 (28), 89 (40), 78
(47), 77 (9). Analysis calculated for C14 HIOCIF 3 N 2 0 2 : C, 50.85; H, 3.05; N, 8.47; Cl, 10.72; F,
17.23. Found: C, 50.83; H, 2.92; N, 8.55; Cl, 10.67; F, 17.14.

N-Benzvl-2-aminothiazole: (Table III, entry 22)

S H Ph
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Free base: light tan crystals, mp 128-130 oC (hexane/Et 2 0). FT-IR (KBr) 3170 (w), 3067 (w), 2971
(w), 2919 (w), 2853 (w), 1570 (s), 1492 (m), 1453 (m), 1351 (m), 1163 (m), 1103 (w), 765 (m), 702
(s), 627 (w), 501 (w) cm- 1; 1H NMR (CDCl3) 8 7.45 - 7.28 (m, 5H), 7.00 (d, J = 3.5 Hz, 1H), 6.46

(d, J = 3.5 Hz, 1H), 6.29 (bs, 1H), 4.46 (s, 2H); 13 C NMR (CDCl3) 8 138.8 (CH), 137.5 (C), 128.6
(CH), 127.6 (CH), 127.6 (CH) 106.3 (CH), 103.0 (C), 49.9 (CH2); El MS n/z (relative intensity) 190

(M+-,41), 106 (8), 91 (100), 65 (24), 39 (12). Analysis calculated for CioH10N 2 S: C, 63.13; H, 5.30;
N, 14.72; S, 16.85. Found: C, 63.01; H, 5.30; N, 14.78; S, 16.85.

N-(Cyclohexvlmethyl-2-aminothiazole: (Table Ell, entry 23)

N?~~
SN'0-
HJ

Free base: light brown crystals, mp 88-90 oC (hexane). FT-IR (KBr) 3183 (s), 3096 (m), 2923 (s),
2847 (s), 1570 (vs), 1499 (s), 1454 (s), 1356 (m), 1317 (m), 1113 (m), 600 (s) cm- 1 ; 1 H NMR

(CDCl3) 8 7.58 (bs, 1H), 7.05 (d, 1H, J = 3.7 Hz), 6.39 (d, 1H, J = 3.7 Hz), 3.03 (d, 2H, J = 6.7

Hz), 1.90-1.80 (m, 2H), 1.80-1.55 (m, 4H), 1.35-1.10 (m, 3H), 1.10-0.90 (m, 2H); 13 C
NMR
(CDCl3) 8 171.8 (C), 138.6 (CH), 104.9 (CH), 53.1 (CH2), 37.5 (CH), 30.9 (CH2), 26.3 (CH2),
25.8 (CH2); El MS n/z (relative intensities) 196 (M+, 23), 113 (92), 100 (100), 86 (34), 55 (41).

Analysis calculated for: C10 H 1 6 N2 S: C, 61.18; H, 8.22; N, 14.27; S, 16.33. Found: C, 60.96; H,
8.13; N, 14.25; S, 16.33.

N-Hexvliminostilbene: (Table III, entry 24)

C,,H13

Free amine: a yellow oil. FT-IR (neat) 3053 (w), 3020 (w), 2929 (s), 2854 (m), 1594 (w), 1559 (w),

1461 (s), 1320 (w), 1240 (m), 1115 (m), 793 (m), 762 (s) cm- 1 ; 1 H NMR (CDCl 3 ) 8 7.31 (dd, J1 =

7.8, J2 = 7.3 Hz, 2H), 7.10-6.90 (m, 6H), 6.79 (s, 2H), 3.76 (t, J = 7.0 Hz, 2H), 1.65-1.50 (m, 2H),
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1.40-1.30 (m, 2H), 1.30-1.15 (m, 4H), 0.91 (t, J = 6.8 Hz, 3H); 13 C NMR (CDCl3) 8 151.1 (C),
133.9 (C), 132.1 (CH), 129.1 (CH), 128.6 (CH), 123.0 (CH), 120.3 (CH), 50.5 (CH2), 31.4 (CH2),
27.5 (CH2), 26.6 (CH2), 22.5 (CH2), 13.9 (CH3); El MS m/z (relative intensity) 277 (M+., 18), 206

(100), 178 (13), 128 (3), 41 (18). Accurate mass calculated for C2 0 H 24 N+: 278.1909. Found:
278.1914.

N-Benzyl-p-toluenesulfonamide: (Table III, entry 26)

CH _ H- CH 2Ph

A white crystalline solid, mp 114-116 oC (EtOAc/hexane). FT-IR (KBr) 3269 (m), 3033 (w), 2916 (w),
1422 (m), 1327 (s), 1161 (s), 1059 (m), 876 (m), 743 (s), 547 (s) cm- 1 ; 1H NMR (free base, CDCl 3 ) 5

7.73 (d, J = 8.3 Hz, 2H), 7.29 - 7.16 (m, 7H), 4.97 (bt, J = 6.0 Hz, 1H), 4.09, (d, J = 6.0 Hz, 2H),
2.42 (s, 3H); 13 C NMR (CDCl 3 ) 8 143.4 (C), 136.7 (C), 136.2 (C), 129.6 (CH), 128.5 (CH), 127.8
(CH), 127.7 (CH), 127.0 (CH), 47.1 (CH 2 ), 21.4 (CH 3 ); CI MS mi/z (relative intensity) 262 (MH+,
100), 189 (6.3), 106 (18), 91 (6.4). Analysis calculated for: C 14 H 15 N0 2 S: C, 64.34; H, 5.79; N, 5.36;
S, 12.27. Found: C, 63.95; H, 5.54; N, 5.33; S, 12.47.

N-(Cyclohexylmethyl)-2,4,6-trichloroaniline:
H Cl

ClCl

Free base: a colorless oil (purified by flash column chromatography on silica gel using 5% Et 2 O in
hexane as eluent). FT-IR (neat) 3401 (w), 2925 (s), 2851 (m), 1559 (w), 1484 (m), 1446 (s), 1381
(w), 1240 (w), 856 (m), 794 (w), 715 (w) cm-1; 1 H NMR (CDCl 3 ) 8 7.21 (s, 2H), 4.04 (s, 1H), 3.15

(d, J = 6.6 Hz, 2H), 1.84-1.60 (m, SH), 1.53-1.42 (m, 1H), 1.30-1.11 (m, 3H), 1.03-0.91 (m, 2H);
13 C NMR
(CDCl 3 ) 8 142.0 (C), 128.6 (CH), 125.6 (C), 124.7 (C), 54.1 (CH 2 ), 38.9 (CH), 30.9

(CH 2 ), 26.5 (CH 2 ), 25.9 (CH 2 ); El MS m/z (relative intensity): 293 (M+, 12), 291 (M+, 13), 258 (2),
212 (31), 211 (12), 210 (100), 209 (15), 208 (97), 197 (5), 195 (6), 145 (5), 136 (5) 109 (5). Analysis
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calculated for Cl 3 HI 6 Cl 3 N: C, 53.36; H, 5.51; N, 4.79; Cl, 36.34. Found: C, 53.41, H, 5.53; N,
4.67; Cl, 36.72.

N-(Cyclohexylmethyl)-2.4-dinitropaniline:
H NO2

NO 2

Free amine: an orange solid, mp 76-78 0 C, purified by flash column chromatography on silica gel using

5% Et 2 O in hexane as eluent followed by trituration with cold hexane. FT-IR (KBr) 3365 (m), 2921

(m), 2849 (m), 1620 (s), 1589 (m), 1527 (m), 1467 (w), 1420 (m), 1338 (s), 1308 (s),1239 (s), 1136

(w), 1069 (w), 744 (w), 663 (w) cm- 1; 1H NMR (CDCl 3 ) 8 9.13 (d, J = 2.4 Hz, 1H), 8.67 (bs, 1H),

8.25 (dd, J1 = 9.6 , J2 = 2.4 Hz, 1H), 6.93 (d, J = 9.6 Hz, 1H), 3.26 (t, J = 6.0 Hz, 2H), 1.89-1.68

(m, 6H), 1.33-1.04 (m, 5H); 13 C NMR (CDCl 3 ) 8 148.6 (C),135.8 (C), 130.3 (CH), 124.4 (CH),

114.0 (CH), 50.0 (CH 2 ), 37.4 (CH), 31.1 (CH 2 ), 26.2 (CH 2 ), 25.7 (CH 2 ); El MS m/z (relative

intensity): 279 (M+, 18), 233 (8), 197 (16), 196 (100), 180 (28), 179 (15), 150 (13), 105 (13), 83 (18),
78 (11), 77 (13). Analysis calculated for C 13H 1 7 N 3 0 4 : C, 55.91; H, 6.14; N, 15.04. Found: C, 55.96;

H, 6.10; N, 15.14.

N-(Cyclohexylmethyl);ert-butyl amine: (Table V, entry 3)

CH 2 -NH- t-Bu

HCI salt: a white solid, mp 241-243 0 C (EtOAc/MeOH). FT-IR (KBr) 3403 (m), 2927 (vs), 2853 (s),

2777 (s), 2622 (w), 2548 (w), 2461 (w), 2410 (w), 1612 (w), 1484 (w), 1447 (w), 1404 (w), 1207
(w), 1190 (w), 1000 (w); IH NMR (DMSO-d6 ) 8 8.69 (bs, 2H), 2.65 (d, J = 12.4 Hz, 2H), 1.47-1.61

(m, 3H), 1.31 (s, 9H), 1.27-1.11 (m, 4H), 0.99-0.90 (m, 2H); 13 C NMR (DMSO-d6) 8 56.3 (C), 46.6

(CH 2 ), 34.8 (CH), 30.4 (CH 2 ), 25.6 (CH2), 25.1 (CH2), 24.9 (CH 3 ); CI MS m/z (relative intensity):
170 (MH+, 8), 168 (15), 155 (6), 154 (55), 114 (22), 112 (18), 86 (100). Accurate mass calculated for
C 11 H24 N+ (MH+): 170.1909. Found: 170.1901+ 0.0015, difference: 4.7 ppm.
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N-Cyclobutyl-4-chlorobenzylamine: (Table V, entry 4)

HCI salt: white crystals, mp 237-238 oC (EtOAc/MeOH). FT-IR (KBr) 2917 (s), 2804 (s), 2762 (s),
2435 (m), 1497 (m), 1432 (m), 1092 (m), 808 (m), 520 (m) cm- 1; 1H NMR (free base, CDC13 ) 8 7.25-

7.22 (m, 4H), 3.64 (s, 2H), 3.28-3.21 (m, 1H), 2.23-2.16 (m, 2H), 1.71-1.63 (m, 4H), 1.38 (bs, 1H);
1H NMR (HCl salt, CDCl 3 + CD 3 0D) 8 9.70 (bs, 1H), 7.50 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 8.4 Hz,

2H), 3.94 (s, 2H), 3.52 (q, J = 8.15 Hz, 1H), 2.95 (bs, 2H), 2.41-2.35 (m, 2H), 2.22-2.13 (m, 2H),
1.99-1.89 (m, 1H), 1.83-1.73 (m, 1H); 13C NMR (free base, CDCl 3 ) 8 138.9 (C), 132.4 (C), 130.1

(CH), 129.4 (CH), 50.2 (CH), 53.4 (CH 2 ), 30.9 (2 CH2 ), 14.6 (CH 2 ); El MS n/z (relative intensity)
196 (M+), 167 (48), 125 (100), 89 (26), 39, (18). Analysis calculated for: C1 1H1 5 Cl 2 N: C, 56.91; H,
6.51; N, 6.03; Cl, 30.54. Found: C, 56.89; H, 6.45; N, 5.87; Cl, 30.82.

trans-N-Benzvl-3-amino-1-phenylpropene: (Table V, entry 5)

H CH2 NHCH2 Ph

Ph H

HCI salt: a white solid, mp 215-216 oC (EtOAc/MeOH). FT-IR (KBr) 2934 (s), 2792 (s), 2600 (m),
2363 (w), 1566 (m), 1495 (m), 1456 (m), 1427 (s), 971 (s), 749 (s), 695 (s) cm- 1 ; 1H NMR (HCI salt,
DMSO-d 6) 8 7.75-7.60 (m, 2H), 7.50-7.30 (m, 8H), 6.80 (d, J = 16.0 Hz, 1H), 6.48 (dt, J1 = 16.0, J2

= 6.9 Hz, 1H), 4.17 (s, 2H), 3.73 (d, J = 6.9 Hz, 2H); 1H NMR (free base, CDC13) 8 7.45-7.10 (m,

10 H), 6.51 (d, J = 15.9 Hz, 1H), 6.29 (dt, J1 = 15.9, J2 = 6.2 Hz, 1H), 3.80 (s, 2H), 3.38 (dd, J1 =
6.2, J2 = 1.2 Hz, 2H), 1.46 (bs, 1H); 13 C NMR (HCI salt, DMSO-d 6 ) 8 138.1 (CH), 137.4 (C), 133.8
(C), 131.9 (CH), 130.5 (CH), 130.3 (CH), 130.1 (CH), 128.3 (CH), 121.9 (CH), 50.8 (CH2), 49.7
(CH2); 13 C NMR (free base, CDC13) 8 140.2 (C), 137.1 (C), 131.3 (CH), 128.5 (CH), 128.4 (CH),
128.3 (CH), 128.1 (CH), 127.3 (CH), 126.9 (CH), 126.2 (CH), 53.3 (CH2), 51.1 (CH2); El MS m/z

(relative intensity) 223 (M+, 11), 133 (9), 132 (82), 130 (10), 118 (10), 117 (26), 115 (28), 105 (25),
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92 (11), 91 (100), 77 (17), 65 (23). Analysis calculated for C16 H 18 CIN: C, 73.98; H, 6.98; N, 5.39;
Cl, 13.65. Found: C, 73.94; H, 6.89; N, 5.34; Cl, 13.72.

4-Cyclopentylmorpholine: (Table V, entry 7)

O N-0

HCI salt * 1.5 H2 0: a white solid, mp 116-120 oC (MeOH). FT-IR (KBr) 3393 (w), 2973 (m), 2924
(m), 2868 (m), 2650 (m), 2603 (m), 2556 (m), 1442 (s), 1264 (s), 1138 (s),1102 (s), 1070 (m), 887
(s), 544 (m), 492 (m), 430 (m) cm- 1 ; 1 H NMR (CDCl3) 8 12.30 (bs, 1H), 4.55-4.40 (m, 1H), 4.35-

4.20 (m, 2H), 4.05- (m, 2H), 3.60-3.30 (m, 3H), 3.15-3.00 (m, 2H), 2.20-2.00 (m, 4H), 2.00-1.80
(m, 2H), 1.75-1.55 (m, 2H); 13 C NMR (CDC13) 8 68.56 (CH), 63.31 (CH2), 51.20 (CH2), 27.39
(CH2), 23.26 (CH2); El MS m/z (relative intensity) 155 (M+, 20), 126 (100), 68 (35), 55 (27), 41 (60).

Analysis calculated for C9 H 18CINO * 1.5 H2 0: C, 49.42; H, 9.68; N, 6.40. Found C, 49.33; H, 9.63;
N, 6.25.