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A Simple Method for Preparation of Secondary Aromatic Amines - I.V. Micovic, M.D. Ivanovic, D.M. Piatak, V.D. Dojic - Synthesis, 1991, p. 1043-1045 - 4-piperidone N-phenethyl-4-piperidone 1-phenethyl-4-piperidone 4-piperidinone NPP ANPP Fentanyl Synthesis Chemistry Manufacture Opioid Opiate Precursors

A Simple Method for Preparation of Secondary Aromatic Amines - I.V. Micovic, M.D. Ivanovic, D.M. Piatak, V.D. Dojic - Synthesis, 1991, p. 1043-1045 - 4-piperidone N-phenethyl-4-piperidone 1-phenethyl-4-piperidone 4-piperidinone NPP ANPP Fentanyl Synthesis Chemistry Manufacture Opioid Opiate Precursors

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A Simple Method for Preparation of Secondary Aromatic Amines - I.V. Micovic, M.D. Ivanovic, D.M. Piatak, V.D. Dojic
Authors: Ivan V. Micovic, M.D. Ivanovic, David M. Piatak, Vera Dj. Dojic
IV Micovic, MD Ivanovic, DM Piatak, VD Dojic
Micovic, IV; Ivanovic, MD; Piatak, DM; Dojic, VD
Micovic IV, Ivanovic MD, Piatak DM, Dojic VD
Synthesis, 1991, 1043-1045
Synthesis, November 1991, Issue 11, Pages 1043-1045
SYNTHESIS, Nov 1991, No. 11, pp 1043-1045
ABSTRACT: A simple and efficient method for the preparation of secondary N-alkylarylamines via reductive amination of ketones with primary aromatic amines using activated zinc/acetic acid is described. It requires only equimolar amounts of starting compounds and affords good yields of the corresponding amines (50-90%). It is not applicable to aldehydes nor aliphatic amines. A large number of methods have been developed to transform a carbonyl moiety to the corresponding amine. Some of the more commonly used procedures involved reduction of carbonyl derivatives, such as imines, enamines, or oxmines, either catalytically or with metal hydrides. Alternatively, a carbonyl compound/amine mixture can often be reduced directly to the corresponding secondary or tertiary amine, utilizing catalytic hydrogenation, formic acid (Leucart-Wallace reaction) or certain metal hydrides. In the latter instance sodium cyanoborohydride appears to be the most convenient reagent due to wide applicability. However, most of the aforementioned procedures require elevated pressure or expensive and toxic reagents. Few aldehydes and acetone have been reductively aminated albeit in low yields with the simpler and inexpensive zinc amalgam and hydrochloric acid, but to our knowledge, it has not been generally applied to carbonyl compounds. It can also effect hydrolysis of various functional groups and decarboxylate β-keto esters. An intramolecular reductive amination of keto anilines to tetrahydroquinolines has been effected by zinc, and 37% hydrobromic acid in acetic acid.
REFERENCES:
Larock, R.C. Comprehensive Organic Transformations, VCH Publishing Inc. New York, 1989, p. 421 J. Org. Chem. 1985, 50, 1916 Billman, J.H.; Tai, K.M. J. Org. Chem. 1958, 23, 535 Yamamoto, H.; Maruoka, K.J. J. Am. Chem. Soc. 1981, 103, 4186 Pojer, P.M. Aust. J. Chem. 1979, 32, 201 Tetrahedron Lett. 1981, 22, 3447 Tetrahedron Lett. 1981, 22, 389 J. Am. Chem. Soc. JACS 1971, 93, 2897 J. Org. Chem. 1985, 50, 1927 Tetrahedron Lett. 1983, 24, 4711 J. Chem. Soc. C, 1966, 531 Journal of Organic Chemistry 1958, 23, 575 J Org Chem 1962, 27, 2209 Journal of the American Chemical Society 1950, 72, 5414 Org. React. 1948, 4, 174 Organic Reactions 1949, 5, 301 Org. Synth. Coll. Vol. 2, 1941, 503 J. Org. Chem. JOC 1968, 33, 1647 Organic Synthesis Collective Volume 6, 1988, 499 J. Org. Chem. 1981, 46, 3571 Synthesis 1984, 603 J. Org. Chem. 1963, 28, 3259 JACS 1969, 91, 3996 Synth. Commun. 1984, 14(13), 1213 Synthesis 1975, 135 (Rev. Review) J Am Chem Soc 1941, 63, 972 J.A.C.S. 1944, 66, 2127 Tetrahedron 1983, 39, 3373 Org Synth, Vol 62, 1984, 14 Journal of the Chemical Society (RSC) 1920, 117, 121 U.S. Patent 2470094 (1949)

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,
A Simple Method for Preparation of Secondary Aromatic Amines - I.V. Micovic, M.D. Ivanovic, D.M. Piatak, V.D. Dojic
Authors: Ivan V. Micovic, M.D. Ivanovic, David M. Piatak, Vera Dj. Dojic
IV Micovic, MD Ivanovic, DM Piatak, VD Dojic
Micovic, IV; Ivanovic, MD; Piatak, DM; Dojic, VD
Micovic IV, Ivanovic MD, Piatak DM, Dojic VD
Synthesis, 1991, 1043-1045
Synthesis, November 1991, Issue 11, Pages 1043-1045
SYNTHESIS, Nov 1991, No. 11, pp 1043-1045
ABSTRACT: A simple and efficient method for the preparation of secondary N-alkylarylamines via reductive amination of ketones with primary aromatic amines using activated zinc/acetic acid is described. It requires only equimolar amounts of starting compounds and affords good yields of the corresponding amines (50-90%). It is not applicable to aldehydes nor aliphatic amines. A large number of methods have been developed to transform a carbonyl moiety to the corresponding amine. Some of the more commonly used procedures involved reduction of carbonyl derivatives, such as imines, enamines, or oxmines, either catalytically or with metal hydrides. Alternatively, a carbonyl compound/amine mixture can often be reduced directly to the corresponding secondary or tertiary amine, utilizing catalytic hydrogenation, formic acid (Leucart-Wallace reaction) or certain metal hydrides. In the latter instance sodium cyanoborohydride appears to be the most convenient reagent due to wide applicability. However, most of the aforementioned procedures require elevated pressure or expensive and toxic reagents. Few aldehydes and acetone have been reductively aminated albeit in low yields with the simpler and inexpensive zinc amalgam and hydrochloric acid, but to our knowledge, it has not been generally applied to carbonyl compounds. It can also effect hydrolysis of various functional groups and decarboxylate β-keto esters. An intramolecular reductive amination of keto anilines to tetrahydroquinolines has been effected by zinc, and 37% hydrobromic acid in acetic acid.
REFERENCES:
Larock, R.C. Comprehensive Organic Transformations, VCH Publishing Inc. New York, 1989, p. 421 J. Org. Chem. 1985, 50, 1916 Billman, J.H.; Tai, K.M. J. Org. Chem. 1958, 23, 535 Yamamoto, H.; Maruoka, K.J. J. Am. Chem. Soc. 1981, 103, 4186 Pojer, P.M. Aust. J. Chem. 1979, 32, 201 Tetrahedron Lett. 1981, 22, 3447 Tetrahedron Lett. 1981, 22, 389 J. Am. Chem. Soc. JACS 1971, 93, 2897 J. Org. Chem. 1985, 50, 1927 Tetrahedron Lett. 1983, 24, 4711 J. Chem. Soc. C, 1966, 531 Journal of Organic Chemistry 1958, 23, 575 J Org Chem 1962, 27, 2209 Journal of the American Chemical Society 1950, 72, 5414 Org. React. 1948, 4, 174 Organic Reactions 1949, 5, 301 Org. Synth. Coll. Vol. 2, 1941, 503 J. Org. Chem. JOC 1968, 33, 1647 Organic Synthesis Collective Volume 6, 1988, 499 J. Org. Chem. 1981, 46, 3571 Synthesis 1984, 603 J. Org. Chem. 1963, 28, 3259 JACS 1969, 91, 3996 Synth. Commun. 1984, 14(13), 1213 Synthesis 1975, 135 (Rev. Review) J Am Chem Soc 1941, 63, 972 J.A.C.S. 1944, 66, 2127 Tetrahedron 1983, 39, 3373 Org Synth, Vol 62, 1984, 14 Journal of the Chemical Society (RSC) 1920, 117, 121 U.S. Patent 2470094 (1949)

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,

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Published by: opiophile on Oct 28, 2010
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