Benzene → Nonivamide

HRID 1109755

Reaction equation

HRID 1109755 reaction equation
Cl.[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[O:11][CH3:12].C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:25](Cl)(=[O:34])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>O>[CH3:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:25]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([OH:2])=[C:4]([O:11][CH3:12])[CH:5]=1)=[O:34]

Participants

6

Reactant 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 69819Nonanoyl chlorideHCID 165576Phenol, 4-(aminomethyl)-2-methoxy-, hydrochloride (1:1)

Product 1

HCID 2998Nonivamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

58.5 parts of 4-hydroxy-3-methoxybenzylamine hydrochloride, 200 parts of benzene and 200 parts of water were charged into a reaction vessel equipped with a three-one motor the rotational frequency of which is variable and an outlet having a stopper at the bottom portion and stirred. 58 parts of potassium carbonate was added to the mixture and further 54 parts of pelargonoyl chloride was added dropwise to the resultant mixture at room temperature. In this state, the mixture was stirred for 3 hours until the end of the reaction. After the stirring was stopped and the mixture was allowed to stand for 30 minutes, the water layer in the lower layer was discharged from the bottom portion. The residue was distilled under a reduced pressure to remove the solvent almost completely, thereby obtaining crude nonylic acid vanillylamide. As a result of quantitative analysis of a slight amount of product by high pressure liquid chromatography (hereinunder referred to as "HPLC"), the purity of nonylic acid vanillylamide was determined to be 91.7%. The irritant nature thereof to skin, especially, to mucosae was strong.

Workup

  1. customequipped with a three-one motor the rotational frequency of which
  2. customan outlet having
  3. stirringIn this state, the mixture was stirred for 3 hours until the end of the reaction
  4. distillationThe residue was distilled under a reduced pressure
  5. customto remove the solvent almost completely

Sources & evidence

ORD record
ord-dfb6d090cce547d4a852dac3e10e03f8
Source dataset
uspto-grants-1994_06
Patent number
US05322862

Linked notes

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