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