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Paper | Regular issue | Vol 41, No. 2, 1995, pp.363-371
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6961
A Facile Synthesis of 6-Amino-1-benzyl-4-methyl- and 6-Amino-1,4-dimethylhexahydro-1H-1,4-diazepines, the Amine Part of Substituted Benzamides with a Potent Serotonin 3 Receptor Antagonistic Activity

Hiroshi Harada, Yoshimi Hirokawa, Toshiya Morie, and Shiro Kato*

*Exploratory Research Laboratories, Dainippon Pharmaceutical Co., Ltd., Enoki 33-94, Suita, Osaka 564, Japan


A facile synthesis of 6-amino-1-benzyl-4-methyl- and 6-amino-1,4-dimethylhexahydro-1H-1,4-diazepines (16a and 16b) which have been served as the amine part of the new and novel benzamides (3 and 4) with a potent serotonin 3 receptor antagonistic activity is reported. The formation of 1,4-diazepine ring system was achieved by the reaction of tris(hydroxymethyl)nitromethane (11) with N,N’-disubstituted ethylenediamines (12a and 12b). The dehydroxymethylation of the resultant 6-hydroxymethyl-6-nitro-1,4-diazepines (13a and 13b) and successive reduction gave the target compounds (16a and 16b), in approximately 15-30% overall yield.