pH dependence of the synthesis of isopelletierine from Δ¹‐piperideine

Abstract

The synthesis of isopelletierine from A'-piperideine and acetoacetic acid was investigated in the p H region 1 to 12. Paper chromatography was used t o analyze the reaction mixtures. Depending on reaction time fair to good yields were obtained over the p H range 2 to 12. The experimental data are discussed in the light of two mechanisms proposed by Schiipf et a12. Several methods have been described for the synthesis of isopelletierine. Except for the synthesis from A'-piperideine, originated by Schiipfl* 2 , and the enzymatic methods described by Clarke and Mann 3, and Tuppy and Faltaous 4 , most of them are lengthy procedures 5 , 6, 7, 8, D.With the ultimate aim of extending the first-named method to the synthesis of derivatives of isopelletierine by using 0x0-acids other than acetoacetic acid l o , a survey has been made of the pH dependence of the reaction.Previous work on this subject has been published by Sch6pJ2, but his study was limited to the pH-range 6-12.