Water → N-[2-(3,4-Dimethoxy-phenoxy)-ethyl]-2-(3,4-dimethoxy-phenyl)-acetamide

HRID 458794Notes

Reaction equation

HRID 458794 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[O:6][CH2:7][CH2:8][NH2:9].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][C:26](Cl)=[O:27])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[O:6][CH2:7][CH2:8][NH:9][C:26](=[O:27])[CH2:25][C:19]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:17]([O:16][CH3:15])[CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3604458(3,4-Dimethoxyphenyl)acetyl chlorideHCID 122988912-(3,4-Dimethoxyphenoxy)ethan-1-amine

Product 1

HCID 18442595N-[2-(3,4-Dimethoxy-phenoxy)-ethyl]-2-(3,4-dimethoxy-phenyl)-acetamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of 2-(3,4-dimethoxy-phenoxy)-ethylamine (2.3 g, 11.8 mmol) in anhydrous THF (21 ml), were added TEA (1.4 ml, 19.2 mmol) and portionwise 3,4-dimethoxyphenylacetylchloride (2.49 g, 11.6 mmol). The resulting mixture was stirred at RT for 20 h under nitrogen. The mixture was combined with H2O and extracted three times with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude solid. Recrystallisation from diethylether gave the title product (3.59 g, 80%) as a white solid.

Workup

  1. extractionextracted three times with CH2Cl2
  2. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid
  6. customRecrystallisation from diethylether

Sources & evidence

ORD record
ord-3bcede50abc0456a8736d17fce9d4915
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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