Synthesis of 5-aminocarbonyl-5H-dibenzo[a,d]cyclohepten-5,10-imine
A powerful new anti-convulsant and anti-ischemic pharmaceutical,5-aminocarbonyl-5H-dibenzo[a,d]cycloheptene-5,10-imine is preparedaccording to a novel synthesis which converts the startingmaterial, commercially available dibenzosubernone to ADCI withoutthe use of chromatographic purification, hazardous reagents orextreme conditions. The starting material is converted to thecorresponding imine through ammonia exposure, and directlyconverted with acetone cyanohydrin in the presence of sodiumcyanide to a 5-amino, 5-cyanocycloheptene intermediate. Theintermediate is cyclized using bromine, followed by a reduction ofthe bromine-carbon bond using sodium cyanoborohydride. The targetcompound is obtained through selective hydrolysis. An overall yieldof 46 percent or better is obtained.
Gonzalez, J., & Carroll, F. (1998). IPC No. U.S.Synthesis of 5-aminocarbonyl-5H-dibenzo[a,d]cyclohepten-5,10-imine (Patent No. 5831095.)