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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.