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Synthesis and N ‐methylation of β‐ 14 C‐ p ‐chloroamphetamine hydrochloride
Author(s) -
Burrows Elizabeth P.,
SandersBush Elaine,
Sekerke H. Joseph,
Smith Howard E.
Publication year - 1976
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580120203
Subject(s) - chemistry , aluminum hydride , nitroethane , hydrochloride , methylation , yield (engineering) , lithium (medication) , medicinal chemistry , lithium aluminium hydride , hydride , condensation , organic chemistry , ion , nitromethane , hydrogen , medicine , biochemistry , materials science , thermodynamics , physics , metallurgy , gene , methoxide , endocrinology
Abstract β‐ 14 C‐ p ‐Chloroamphetamine hydrochloride was prepared by condensation of carbonyl‐ 14 C‐ p ‐chlorobenzaldehyde with nitroethane followed by lithium aluminum hydride (LAH) reduation of the resulting chloro‐phenylnitropropene. After purfication the overall yield was about 25%. N‐Methyl‐ and N,N‐dimethyl‐ β‐ 14 C‐ p ‐chloroamphetamine were prepared, respectively, by LAH reduction of N ‐carbobenzoxy – β‐ 14 C‐ p ‐chlorpamphetamine and by reductive (Eschweiler‐Clarke methylation of β‐ 14 C‐ p ‐ Chlolroamphetamine.