(3,4-Dimethoxyphenyl)acetic acid → N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 1490323Notes

Reaction equation

HRID 1490323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](Cl)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(CC(O)=O)C=CC=1OC.S(Cl)(Cl)=O.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[CH2:38][CH2:39][NH2:40].[OH-].[Na+]>C(Cl)(Cl)Cl.ClCCl>[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[CH2:38][CH2:39][NH:40][C:12](=[O:13])[CH2:11][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 8421HomoveratrylamineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 67318N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A dry dichloromethane solution (1000 ml) of 3,4-dimethoxyphenylacetyl chloride prepared from 325 g of 3,4-dimethoxyphenylacetic acid and 300 ml of thionyl chloride was slowly added to a two-phase solvent consisting of 300 g of 3,4-dimethoxyphenethylamine, 850 ml of 2N sodium hydroxide, and 2000 ml of dichloromethane while stirring under ice-cooling. Chloroform was added to the mixture to dissolve the precipitated solid. The aqueous layer was removed, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution, dried, and the solvent was evaporated. To the residue was added methanol, the mixture was heated and allowed to cool, and the thus precipitated crystal was collected by filtration to yield 570 g of the title compound.

Workup

  1. additionwas slowly added to a two-phase solvent
  2. temperaturecooling
  3. dissolutionto dissolve the precipitated solid
  4. customThe aqueous layer was removed
  5. washthe organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution
  6. customdried
  7. customthe solvent was evaporated
  8. additionTo the residue was added methanol
  9. temperaturethe mixture was heated
  10. temperatureto cool
  11. filtrationthe thus precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-4653356e14bc45a492a29087fb22129e
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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