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Journal of pharmaceutical sciences

Journal of pharmaceutical sciences

IF: 3.7
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2-(Methylamino)-5-chlorobenzophenone Imine: A Novel Product Formed in Base-Catalyzed Hydrolysis of Diazepam

Published:1 July 1996 DOI: 10.1021/js9504245 PMID: 8819000
Shen K. Yang, Ren Tang, Tian Jian Yang, Quan-Long Pu, Ziping Bao

Abstract

Diazepam (1), a hypnotic and anxiolytic drug in worldwide use, formed an intermediate product in a mixture of ethanol and sodium hydroxide ([NaOH] ≥ 1 M). The intermediate product slowly decomposed to form 2-(methylamino)-5-chlorobenzophenone imine (2) and 2-(methyl-amino)-5-chlorobenzophenone (3). The amount of 2 formed, relative to that of 3, increased with increasing NaOH concentration. Compound 2, a heretofore unknown derivative of 1, was characterized by high-performance liquid chromatography, ultraviolet–visible absorption, mass, and proton nuclear magnetic resonance spectral analyses.

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