Chloride → Capsaicin

Participants

Reaction Steps

By using a similar reaction vessel to that in Example 9, 5.7 parts of 8-methylnon-trans-6-enoyl chloride and 0.2 part of pyridine were added to a solution of 4.7 parts of 4-hydroxy-3-methoxybenzylamine in 25 parts of diethyl ether, and the mixture was stirred at room temperature for 4 hours. After 10 parts of water was added to the mixture and stirred for 5 minutes, the resultant mixture was allowed to stand for 5 minutes. The water layer in the lower layer was discharged. By almost completely removing ether under a reduced pressure, crude (E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide was obtained. As a result of quantitative analysis of a slight amount of product by an HPLC, the purity of (E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide was determined to be 90.5%. The irritant nature thereof to skin, especially, to mucosae was strong as nonylic acid vanillylamide obtained in Example 9.

Provenance & Evidence