The reduction of Schiff bases; N-benzylidene- and N-(1-phenylethylidene)arylamines with zinc borohydride in diethyl ether gave the corresponding amines in excellent yield. Af-benzylidene-benzyl- and cyclohexylamine, N-(1-phenylethylidene)- and N-(cyclohexyl-idene)cyclohexylamines, however, require additional treatment with 6N HCl to liberate the amine-borane complex to give the corresponding amines in quanitative yield. The procedure was also applied in the tandem alkylation-reduction of nitriles to yield 1-phenylalkylamines in good yield.
ASJC Scopus subject areas
- Organic Chemistry