A Mild Reduction of Azomethines with Zinc Borohydride. Synthetic Application to Tandem Alkylation-Reduction of Nitriles

Article abstract of DOI:10.1055/s-1990-26886

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.N-benzylidene-benzyl- and cyclohexylamine, N-(1-phenylethylidene)- and N-(cyclohexylidene)cyclohexylamines, however, require additional treatment with 6 N HCl to liberate the amine-borane complex to give the corresponding amines in quantitative yield.The procedure was also applied in the tandem alkylation-reduction of nitriles to yield 1-phenylalkylamines in good yield.