Triethylamine → n-(2,2-Dimethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 648953Notes

Reaction equation

HRID 648953 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].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH2:19].C(N(CC)CC)C>C(Cl)Cl>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH:19][C:12](=[O:13])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 13092500n-(2,2-Dimethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While cooling with ice, a solution of 3,4-dimethoxyphenylacetic acid chloride (485.2 g) in methylene chloride (1.1 liters) is added dropwise at 15°-20° C. to a solution of aminoacetaldehyde dimethylacetal (246.2 ml) and triethylamine (315 ml) in methylene chloride (2.2 liters) and the resulting mixture is stirred for 1 hour at 16°-18° C. It is then extracted several times with water, dried over magnesium sulphate and concentrated by evaporation. The resulting oil slowly crystallizes out.

Workup

  1. temperatureWhile cooling with ice
  2. extractionIt is then extracted several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated by evaporation
  5. customThe resulting oil slowly crystallizes out

Sources & evidence

ORD record
ord-730a2bc9fa9e47809b6c87f110589fb2
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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