Bucherer Berg's Reaction of $\alpha$-Piperidinoacetophenone in the Formation of Hydantoin

$\alpha$-Piperidinoacetophenone의 Hydantoin 형성 반응

In Bucherer-Berg's reaction of $\alpha$-piperidinoacetophenone with KCN and ($NH_{4})_{2}CO_{3}$ in dilute alcohol solution to form hydantoin, the expected 5-phenyl-5-piperidinomethylhydantoin was not formed. In this reaction $\alpha$-piperidinomethyl group was eliminated and 5-phenylhydantoin was obtained. According to GC/MS study of the reaction mixture, the one of the chromatograms, which has mole peak 124, was identified as a-piperidinoacetonitrile. Under the pressurized condition, diphenylhydantil was obtained instead of 5-phenylhydantoin, which might have dimerized to the former.