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Synthesis 1990; 1990(5): 401-402
DOI: 10.1055/s-1990-26886
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A Mild Reduction of Azomethines with Zinc Borohydride. Synthetic Application to Tandem Alkylation-Reduction of Nitriles

Hiyoshizo Kotsuki* , Naka Yoshimura, Isao Kadota, Yasuyuki Ushio, Masamitsu Ochi
  • *Department of Chemistry, Faculty of Science, Kochi University, Akebono-cho, Kochi 780, Japan
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Publication Date:
17 September 2002 (online)

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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 quanitative yield. The procedure was also applied in the tandem alkylation-reduction of nitriles to yield 1-phenylalkylamines in good yield.