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Psychotropic derivatives of 5-phenyl-7-chloro-1,3-dihydro-1,4-benzodiazepin-2-one and contribution to the synthesis of its 5-(2-chlorophenyl) analogue

1980; Wiley-VCH; Volume: 45; Issue: 12 Linguagem: Inglês

10.1135/cccc19803593

1212-6950

Z. J. Vejdělek, M. Rajšner, A Dlabac, Miroslav Ryska, J. HOLUBEK, E. SVATEK, M. PROTIVA,

Coordination Chemistry and Organometallics

Alkylation of 7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one ( I ) with 2,5-dimethoxyphenacyl bromide and 3-(4-phenylpiperazino)propyl chloride afforded the N-substituted derivatives of nordazepam III and IV ; compound IV revealed properties of a potential hypnotic agent. Reaction of 4-chloronitrobenzene with (2-chlorophenyl)acetonitrile in methanolic solutions of alkali hydroxides gave mixtures from which the following compounds were isolated: 5-chloro-3-(2-chlorophenyl)-2,1-benzisoxazole ( VII ), the O-methyloxime X , 5-chloro-2,3-bis(2-chlorophenyl)indole ( XI ), 2-chloro-4'-nitrobenzophenone ( XVII ) and 2-chloro-9-cyanoacridine N-oxide ( XX ). A similar reaction of 4-chloronitrobenzene with (2-fluorophenyl)acetonitrile gave compound XX as the main product; in smaller amounts 4-nitroanisole, 2-fluoro-4'-nitrobenzophenone ( XVIII ) and 2-chloroacridine-9-carbonitrile ( XXIV ) were obtained. Compound VII was reduced to the aminobenzophenone derivative V which was transformed via the phthalimidoacetyl derivative VI to the chlorodemethyldiazepam II .