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

HRID 2290209Notes

Reaction equation

HRID 2290209 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

A solution of 485.2 gm of 3,4-dimethoxyphenylacetyl chloride in 1.1 liters of methylene chloride is added dropwise at 15° to 20° C. to a solution of 246.2 ml of aminoacetaldehyde dimethylacetal and 315 ml of triethylamine in 2.2 liters of methylene chloride, while the mixture is cooled with ice, and then the mixture is stirred for a further hour at 16° to 18° C. It is then extracted several times with water, dried over magnesium sulfate, and concentrated by evaporation. The resulting oil slowly crystallizes out.

Workup

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

Sources & evidence

ORD record
ord-c4500cf39834418cb0afff71b6c260b6
Source dataset
uspto-grants-1986_10
Patent number
US04616011

Reaction notes

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