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Amine Dealkylations with Acyl Chlorides - J.H. Cooley & E.J. Evain - Synthesis, 1989(1), p. 1-7

Amine Dealkylations with Acyl Chlorides - J.H. Cooley & E.J. Evain - Synthesis, 1989(1), p. 1-7

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Amine Dealkylations with Acyl Chlorides
Authors: J. H. Cooley and E. J. Evain
Journal: Synthesis
Synthesis 1989(1): 1-7
Synthesis, 1989, No. 1, 1-7
DOI: 10.1055/s-1989-27129
Cooley, J. H.; Evian, E. J. Synthesis 1989, 1
https://www.thieme-connect.de/DOI/DOI?10.1055/s-1989-27129
ABSTRACT: The use of cyanogen bromide to dealkylate tertiary amines is known as the von Braun reaction. More recently, the development of carbonochloridate (chloroformate) reagents to effect these N-dealkylations has reached such high yields and mild reaction conditions as to open up the possibility of using simple alkyl groups to protect secondary amines. If an acyl chloride moiety is introduced within the molecule containing the tertiary amine, either by reaction of an organic acid with thionyl chloride or by treatment of a diamine with phosgene, intramolecular cyclization-N-dealkylation results leading to novel products. 1. Introduction 2. Kinetic and Mechanistic Aspects 3. Isolation of the Intermediate Salts 4. N-Dealkylations 5. Cyclization-Dealkylation Reactions 6. Summary and Outlook
11. Olofson, Tetrahedron Lett, 1977, 1567
13. JACS, 1955, 77, 3104
14. Tetrahedron Lett, 1983, 3233
15. Olofson, J. Org. Chem. 1984, 49, 2081
16. Tetrahedron Lett. 1969, 3039
17. Tetrahedron Lett. 1966, 1375
18. Tetrahedron Lett. 1969, 635
19. Tetrahedron Lett. 1968, 4549
23. J. Med. Chem. 1964, 7, 302
24. US Patent # 3337580 (1967)
25. J Heterocyclic Chem. 1964, 1, 186
26. Tetrahedron Lett. 1982, 2829
27. J. Org. Chem. 1983, 48, 5074
28. Bull. Soc. Chim. Belg. 1985, 94, 457

structure-activity relationships, SARs, analgetics, acetylfentanyl, 3-methylfentanyl, 3MF, TMF, AMF, alphamethylfentanyl, Ohmefentanyl, beta-hydroxy, alpha-methyl, Mefentanyl, 4-methoxymethylcarbonyl, 4-methoxycarbonyl, 4-substituted piperidines, 4,4-disubstituted piperidines, 4-piperidines, 4-substituted, 4,4-disubstituted, fentanil, phentanyl, phentanil, N-phenylethyl-4-piperidones, piperid-4-ones, N-phenylethyl-4-piperidinones, piperidin-4-ones, NPP, ANPP, Sigfreid Sigfried fentanyl opioid opiate synthesis, mu u delta d Kappa K opioid receptor, opiate alkaloid, poppy alkaloids, subutex, suboxone, reducing agents, LiAlH4, lithium aluminum hydride, sodium borohydride, platinum oxide, catalytic hydrogenation, N-debenzylation, morphine-like, Paul A.J. PAJ Adrian Jan Janssen, Pharmaceuticals, pharma, Pharmacy, pharmacology, pharamcokinetics, P. Papaver somniferum, dipipanone, phenadoxone, 4-phenylpiperidines, organic synthesis, novel organic synthesis, 4-anilinopiperidine 4-propionanilinopiperidine 4-anilidopiperidine 4-propionanilidopiperidine chemistry, piperidine nitrogen chemistry, organic heterocyclic nitrogen compounds, opioid chemistry, opioid synthesis, chemical syntheses, pseudoephedrine, ephedra, phenylacetone, phenyl-2-propanone, P2P, methylamine, MDMA, MDA, methamphetamine amphetamine synthesis manufacture precursors, saffrole oil, methylenedioxymethamphetamne, ecstasy, x, XTC, ADAM, EVE, Alexander T. Shulgin, PiHKAL: A Chemical Love Story, TiHKAL, 2-CE, 2-CB, 2-CI, 2CE 2CI 2CB, PEA, phenylethylamines, psychoactive drugs, psychedelic, psychogenic, psychotropic, phenethylamines, Sympathomimetic amines, dopaminergic, serotonin, norepinephrine, noradrenaline, adrenaline, dopamine, catecholamines, central sympathetic parasympathetic nervous system, sympatholytics, parasympatholytics, anxiolytics, diuresis, diuretics, methyltestosterone, 5-alpha-reductase inhibitor, testosterone, dihydrotestosterone, PDE5, viagra, cialis, levitra, Sildenafil citrate, tadalafil, vardenafil, cGMP-specific phosphodiesterase type 5, BPH, benign prostate hyperplasia, avodart, Dutasteride CNS, SSRI, antidepressants, prozac, paxil, Zoloft, venlafaxine, fluoxetine, fluvoxamine, SNRI, Bupropion, Wellbutrin, Zyban, oxirane, MOR, DOR, KOR, naloxone, naltrexone, DXM, dextromethorphan, levorphanol, dextropropoxyphene, dextromoramide, phenacyl, arylmorphan, azabicyclo, azaprocin mixed partial agonist antagonist, bindin
Amine Dealkylations with Acyl Chlorides
Authors: J. H. Cooley and E. J. Evain
Journal: Synthesis
Synthesis 1989(1): 1-7
Synthesis, 1989, No. 1, 1-7
DOI: 10.1055/s-1989-27129
Cooley, J. H.; Evian, E. J. Synthesis 1989, 1
https://www.thieme-connect.de/DOI/DOI?10.1055/s-1989-27129
ABSTRACT: The use of cyanogen bromide to dealkylate tertiary amines is known as the von Braun reaction. More recently, the development of carbonochloridate (chloroformate) reagents to effect these N-dealkylations has reached such high yields and mild reaction conditions as to open up the possibility of using simple alkyl groups to protect secondary amines. If an acyl chloride moiety is introduced within the molecule containing the tertiary amine, either by reaction of an organic acid with thionyl chloride or by treatment of a diamine with phosgene, intramolecular cyclization-N-dealkylation results leading to novel products. 1. Introduction 2. Kinetic and Mechanistic Aspects 3. Isolation of the Intermediate Salts 4. N-Dealkylations 5. Cyclization-Dealkylation Reactions 6. Summary and Outlook
11. Olofson, Tetrahedron Lett, 1977, 1567
13. JACS, 1955, 77, 3104
14. Tetrahedron Lett, 1983, 3233
15. Olofson, J. Org. Chem. 1984, 49, 2081
16. Tetrahedron Lett. 1969, 3039
17. Tetrahedron Lett. 1966, 1375
18. Tetrahedron Lett. 1969, 635
19. Tetrahedron Lett. 1968, 4549
23. J. Med. Chem. 1964, 7, 302
24. US Patent # 3337580 (1967)
25. J Heterocyclic Chem. 1964, 1, 186
26. Tetrahedron Lett. 1982, 2829
27. J. Org. Chem. 1983, 48, 5074
28. Bull. Soc. Chim. Belg. 1985, 94, 457

structure-activity relationships, SARs, analgetics, acetylfentanyl, 3-methylfentanyl, 3MF, TMF, AMF, alphamethylfentanyl, Ohmefentanyl, beta-hydroxy, alpha-methyl, Mefentanyl, 4-methoxymethylcarbonyl, 4-methoxycarbonyl, 4-substituted piperidines, 4,4-disubstituted piperidines, 4-piperidines, 4-substituted, 4,4-disubstituted, fentanil, phentanyl, phentanil, N-phenylethyl-4-piperidones, piperid-4-ones, N-phenylethyl-4-piperidinones, piperidin-4-ones, NPP, ANPP, Sigfreid Sigfried fentanyl opioid opiate synthesis, mu u delta d Kappa K opioid receptor, opiate alkaloid, poppy alkaloids, subutex, suboxone, reducing agents, LiAlH4, lithium aluminum hydride, sodium borohydride, platinum oxide, catalytic hydrogenation, N-debenzylation, morphine-like, Paul A.J. PAJ Adrian Jan Janssen, Pharmaceuticals, pharma, Pharmacy, pharmacology, pharamcokinetics, P. Papaver somniferum, dipipanone, phenadoxone, 4-phenylpiperidines, organic synthesis, novel organic synthesis, 4-anilinopiperidine 4-propionanilinopiperidine 4-anilidopiperidine 4-propionanilidopiperidine chemistry, piperidine nitrogen chemistry, organic heterocyclic nitrogen compounds, opioid chemistry, opioid synthesis, chemical syntheses, pseudoephedrine, ephedra, phenylacetone, phenyl-2-propanone, P2P, methylamine, MDMA, MDA, methamphetamine amphetamine synthesis manufacture precursors, saffrole oil, methylenedioxymethamphetamne, ecstasy, x, XTC, ADAM, EVE, Alexander T. Shulgin, PiHKAL: A Chemical Love Story, TiHKAL, 2-CE, 2-CB, 2-CI, 2CE 2CI 2CB, PEA, phenylethylamines, psychoactive drugs, psychedelic, psychogenic, psychotropic, phenethylamines, Sympathomimetic amines, dopaminergic, serotonin, norepinephrine, noradrenaline, adrenaline, dopamine, catecholamines, central sympathetic parasympathetic nervous system, sympatholytics, parasympatholytics, anxiolytics, diuresis, diuretics, methyltestosterone, 5-alpha-reductase inhibitor, testosterone, dihydrotestosterone, PDE5, viagra, cialis, levitra, Sildenafil citrate, tadalafil, vardenafil, cGMP-specific phosphodiesterase type 5, BPH, benign prostate hyperplasia, avodart, Dutasteride CNS, SSRI, antidepressants, prozac, paxil, Zoloft, venlafaxine, fluoxetine, fluvoxamine, SNRI, Bupropion, Wellbutrin, Zyban, oxirane, MOR, DOR, KOR, naloxone, naltrexone, DXM, dextromethorphan, levorphanol, dextropropoxyphene, dextromoramide, phenacyl, arylmorphan, azabicyclo, azaprocin mixed partial agonist antagonist, bindin

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Published by: jtjdp4 on Oct 19, 2010
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