Chloride → Capsaicin

HRID 1109757Notes

Reaction equation

HRID 1109757 reaction equation
[Cl-].N1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][C:10]=1[O:17][CH3:18].[OH2:19]>CCOCC>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:14][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7]/[CH:10]=[CH:11]/[CH:12]([CH3:15])[CH3:13])=[CH:11][C:10]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 312ChlorideHCID 962Water2×HCID 1049PyridineHCID 70966Vanillylamine

Product 1

HCID 1548943Capsaicin

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  1. stirringstirred for 5 minutes
  2. waitto stand for 5 minutes

Sources & evidence

ORD record
ord-3b4bf168862647c7855154e1d4d340c9
Source dataset
uspto-grants-1994_06
Patent number
US05322862

Reaction notes

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