Reactions of alpha -aminonitriles. IV. Dimerization of alpha -piperidinoacetonitrile with tert-butylmagnesium chloride

Abstract

alpha -Piperi-dinoacetonitrile (I) (0.2 mole) in 200 ml. Et2O was treated with 0.4 mole tert-BuMgCl in 500 ml. Et2O with cooling 2 hrs. to give 70% 3-amino-2,4-dipiperidinocrotononitrile (II), m. 86-7 Deg. With half the above amts. of reagents, II was obtained in 90% yield, and 0.054 mole isobutane was collected. The isobutane was identified by gas chromatog. in 30% benzyl ether on C22 firebrick with H as carrier gas at 40 Deg. The ir spectrum of II is reported and the mechanism of II formation is discussed. I was also treated with tert-BuONa in PhMe to give 19.4% II.