Tetrahedron

Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H 2 O/CHCl 3 system

B Wang, F Yang, YF Shan, WW Qiu, J Tang

Index: Wang, Bo; Yang, Fan; Shan, Yi-Fan; Qiu, Wen-Wei; Tang, Jie Tetrahedron, 2009 , vol. 65, # 27 p. 5409 - 5412

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Citation Number: 13

Abstract

Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4–C18 aliphatic or aromatic acyl chlorides, the yields were up to 93–96% with high purity after a simple work-up procedure, and only 1–1.16 equiv of acyl chloride was needed in the reaction.