Acetyl chloride → N-Acetyl-3,4-dimethoxyphenethylamine

HRID 35220

Reaction equation

HRID 35220 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>C(Cl)(Cl)Cl>[C:21]([NH:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8421HomoveratrylamineHCID 8471Triethylamine

Product 1

HCID 80465N-Acetyl-3,4-dimethoxyphenethylamineYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of β-(3,4-dimethoxyphenyl)ethylamine (100 g, 0.552 m) and triethylamine (66.6 g, 0.66 m) in CHCl3 (1 liter) was added acetyl chloride (47.1 g, 0.60 mole) dropwise over a period of 30 min. and the mixture stirred overnight. The mixture was washed with 3×500 ml H2O, dried over MgSO4 and evaporated to a solid. The solid was dissolved in 500 ml hot CCl4, 300 ml cyclohexane added and allowed to cool slowly. The crystallized solid was collected by filtration and dried to afford N-acetyl-3,4-dimethoxyphenethylamine as a white solid, 112.1 g (91% yield). m.p. 99°-100°.

Workup

  1. washThe mixture was washed with 3×500 ml H2O
  2. dry with materialdried over MgSO4
  3. customevaporated to a solid
  4. dissolutionThe solid was dissolved in 500 ml hot CCl4
  5. addition300 ml cyclohexane added
  6. temperatureto cool slowly
  7. filtrationThe crystallized solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-065da7d29c6a4004af6a0f69b6e44623
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Linked notes

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