SYNTHESIS OF ALPHA-AMINONITRILES BY SELF-CATALYZED, STOICHIOMETRIC REACTION OF PRIMARY AMINES, ALDEHYDES, AND TRIMETHYLSILYL CYANIDE

Alpha-Aminonitriles can be prepared at room temperature in good yield by either the addition of a primary amine to a mixture aldehyde/trimethylsilyl cyanide (TMSCN) or by the addition of an aldehyde to a mixture amine/TMSCN. The reaction proceeds via the initial condensation of a minute amount of aldehyde and amine groups to generate azomethine bonds and water. The latter then acts catalytically to rapidly convert the aldehyde into the trimethylsilyl cyanohydrin, which then undergoes nucleophilic attack by the amine. Several new alpha-aminonitriles and bis(alpha-aminonitrile)s have been prepared.