Potential antidepressants. Synthesis of 6,11-dihydrodibenzo[b,e]thiepin-11-yl (dimethylaminomethyl)phenyl ethers, sulfides, amines and some related compounds

Abstract

Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-bromo derivative with the isomeric (dimethylaminomethyl)phenols, (dimethylaminomethyl)thiophenols, and (dimethylaminomethyl)anilines in toluene afforded the title compounds IIIb,c, Va, VIIIa,b,c, and Xa,b,c. Reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin and its 2-chloro and 2-methyl derivatives with N,N-dimethyl-2-(4-aminophenoxy)ethylamine and N,N-dimethyl-3-(4-aminophenoxy)propylamine by heating in dimethylformamide in the presence of sodium carbonate gave the diamino ethers XI-XIV. The compounds showed only indications of the antidepressant agents profile and some antimicrobial effects in vitro.