5-Phenylhydantoin의 아미노메칠화 반응

Aminomethylation of 5-Phenylhydantoin

The behavior of the 5-phenylhydantoin (5-phenyl-2,4-imidazolidinedione) ring in the aminomethylation reaction was studied in order to determine the orientation of this substitution. In case of monoaminomethylation, 3-morpholinomethyl-5-phenylhydantoin (or 3-piperidinomethyl-5-phenylhydantoin) was synthesized by the condensation of 5-phenylhydantoin with one mole of morpholine (or piperidine) and one mole of formaldehyde. 1,3-Dimorpholinomethyl-5-phenylhydantoin was obtained in the attempted condensation of 5-phenylhydantoin with two moles of morpholine and two moles of formaldehyde. Despite the close resemblance to morpholine the attempted condensation of 5-phenylhydantoin with piperidine and formaldehyde under reflux gave no expected 1, 3-dipiperidinomethyl-5-phenylhydantoin. In case of diaminometbylation using piperidine and formaldehyde, only 3,5-dipiperidinomethyl-5-phenylhydantoin was formed.