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Micellar Catalysis of Organic Reactions. 18. Basic Hydrolysis of Diazepam and Some N-Alkyl Derivatives of Nitrazepam
Broxton, Trevor J.,Wright, Sallyanne
, p. 2965 - 2969 (2007/10/02)
Kinetic and mechanistic studies of the basic hydrolysis of several benzodiazepinone drugs have been carried out in the presence of micelles of cetyltrimethylammonium bromide (CTAB) and in aqueous solution.For diazepam, a change of mechanism from initial azomethine hydrolysis in water to initial amide hydrolysis in the presence of micelles of CTAB is indicated.For nimetazepam and N-benzylnitrazepam, initial amide hydrolysis was observed both in the presence of CTAB and in water.For the latter compounds, strong catalysis (50-100) of amide hydrolysis (phase 1) by micelles of CTAB was observed, while azomethine hydrolysis (phase 2) was only very weakly catalyzed (3-4-fold).For diazepam, the catalysis was smaller (9-18-fold), but this was accompanied by a mechanistic change so that here the actual catalysis of amide hydrolysis is masked.
