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

HRID 35220

Reaktionsgleichung

Reaktionsgleichung von HRID 35220
[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]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8421HomoveratrylamineHCID 8471Triethylamine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-065da7d29c6a4004af6a0f69b6e44623
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766131

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