Homoveratrylamine → 2-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamide

HRID 848728Notes

Reaction equation

HRID 848728 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][NH2:8].[C:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[NH:24][CH2:25][C:26](O)=[O:27])(=[O:16])[NH2:15]>C(Cl)(Cl)Cl>[C:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[NH:24][CH2:25][C:26]([NH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:27])(=[O:16])[NH2:15]

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 20564281N-(2-carbamoyl-5-chlorophenyl)glycine

Product 1

HCID 100918812-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamideYield 56.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.36 g of 3,4-dimethoxyphenethylamine was added 0.46 g of N-(2-carbamoyl-5-chlorophenyl)glycine and the mixture was stirred at 175° to 185° C. for 6 hours under nitrogen atmosphere. After cooling, the mixture was dissolved in 50 ml of chloroform and the chloroform solution was filtered to remove insoluble materials. The filtrate was washed with 5% hydrochloric acid, a 5% aqueous sodium carbonate solution and water and then dried. The solvent was evaporated in vacuo, and the residue was subjected to column chromatography on silica gel (15 g) and eluted with a mixture of chloroform and methanol (50:1 by volume). The eluate was concentrated to give 0.44 g of 2-(2-carbamoyl-5-chlorophenylamino)-N-(3,4-dimethoxyphenethyl)acetamide as colorless needles having a melting point of 167.5°-169° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe chloroform solution was filtered
  3. customto remove insoluble materials
  4. washThe filtrate was washed with 5% hydrochloric acid
  5. dry with materiala 5% aqueous sodium carbonate solution and water and then dried
  6. customThe solvent was evaporated in vacuo
  7. washeluted with a mixture of chloroform and methanol (50:1 by volume)
  8. concentrationThe eluate was concentrated

Sources & evidence

ORD record
ord-85a476f0c50c4da49095a556ec2b89e2
Source dataset
uspto-grants-1981_10
Patent number
US04297357

Reaction notes

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