Synthesis of 5-aminocarbonyl-5H-dibenzo[a,d]cyclohepten-5,10-imine

Abstract

A powerful new anti-convulsant and anti-ischemic pharmaceutical, 5-aminocarbonyl-5H-dibenzo[a,d]cycloheptene-5,10-imine is prepared according to a novel synthesis which converts the starting material, commercially available dibenzosubernone to ADCI without the use of chromatographic purification, hazardous reagents or extreme conditions. The starting material is converted to the corresponding imine through ammonia exposure, and directly converted with acetone cyanohydrin in the presence of sodium cyanide to a 5-amino, 5-cyanocycloheptene intermediate. The intermediate is cyclized using bromine, followed by a reduction of the bromine-carbon bond using sodium cyanoborohydride. The target compound is obtained through selective hydrolysis. An overall yield of 46 percent or better is obtained.