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Abstract
alpha -Piperidinoacetonitrile (I) was treated with BuMgCl in the ratio 2:1-1:2 and allowed to react for 20 min. or 2 hrs. to give 28-43% 3-amino-2,4-dipiperidinocrotononitrile (II). The yield of II was affected more by the ratio of the reagents than by the reaction time. The other product was 1-piperidino-2-hexanone (III), b15 120 Deg. The formation of II proceeds by addn. of BuMgCl to I, addn. ...
Abstract
alpha -Piperidinoacetonitrile (I) was treated with BuMgCl in the ratio 2:1-1:2 and allowed to react for 20 min. or 2 hrs. to give 28-43% 3-amino-2,4-dipiperidinocrotononitrile (II). The yield of II was affected more by the ratio of the reagents than by the reaction time. The other product was 1-piperidino-2-hexanone (III), b15 120 Deg. The formation of II proceeds by addn. of BuMgCl to I, addn. of a second mol. of I, followed by a second mol. of BuMgCl and hydrolysis of the complex to give II, C4H10, and Mg(OH)Cl. A similar addn. of 2 mols. BuMgCl to I is proposed for the formation of III.
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