2-(methylamino)-5-chlorobenzophenone imine: a novel product formed in base-catalyzed hydrolysis of diazepam.
Diazepam (1), a hypnotic and anxiolytic drug in worldwide use, formed an intermediate product in a mixture of ethanol and sodium hydroxide ([NaOH] > or = 1 M). The intermediate product slowly decomposed to form 2-(methylamino)-5-chlorobenzophenone imine (2) and 2-(methylamino)-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.
Yang
S K
SK
Department of Pharmacology, F. Edward Hébert School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, MD 20814-4799, USA.
Tang
R
R
Yang
T J
TJ
Pu
Q L
QL
Bao
Z
Z
D001577:Benzophenones / Q000378:metabolism*; D002384:Catalysis; D003975:Diazepam / Q000378:metabolism*; D006868:Hydrolysis; D007700:Kinetics; D013056:Spectrophotometry, Ultraviolet; D014867:Water / Q000737:chemistry
D001577:Benzophenones; D014867:Water; C103497:2-(methylamino)-5-chlorobenzophenone imine; D003975:Diazepam