Reduction with organic selenium compounds II. Reduction of Schiff bases with selenophenol reductive alkylation of amines with carbonyl compounds

Reduction of Schiff bases with selenophenol proceeded at room temperature to yield the corresponding sec. amines quantitatively. The reaction of either prim. amine or sec. amine with carbonyl compound and selenophenol gave sec. or tert. amines, respectively. Different alkyl groups can be introduced successively on nitrogen of prim. amines to afford tert. amines bearing three different alkyl groups desired by one pot reaction.