Homoveratrylamine → N-[2-(3,4-dimethoxyphenyl)-ethyl]-2-hydroxy-2-(4-methoxyphenyl)ethylamine

HRID 596613

Reaktionsgleichung

Reaktionsgleichung von HRID 596613
[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].[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([CH:20]2[O:22][CH2:21]2)=[CH:18][CH:17]=1>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:21][CH:20]([OH:22])[C:19]2[CH:23]=[CH:24][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

4

Edukt 2

HCID 8421HomoveratrylamineHCID 980482-(4-Methoxyphenyl)oxirane

Produkt 1

HCID 12668014N-[2-(3,4-dimethoxyphenyl)-ethyl]-2-hydroxy-2-(4-methoxyphenyl)ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A mixture of 16 g. (88 mmol) of 3,4-dimethyoxyphenylethylamine and 13.5 g. (88 mmol) of p-methoxystyrene oxide is heated with stirring under argon on a steam bath overnight. A sample is withdrawn from the reaction mixture and chromatographed on a silica column, eluting with benzene ethyl acetate to isolate the pure product in crystalline form. To the remainder of the reaction mixture is added 100 ml. of ethyl acetate-hexane (1:1) and seeded with the crystalline product, with stirring and chilling. Filtration furnishes the product N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-methoxyphenyl)ethylamine, m.p. 92° C.

Aufarbeitung

  1. additionA mixture of 16 g
  2. customA sample is withdrawn from the reaction mixture
  3. customchromatographed on a silica column
  4. washeluting with benzene ethyl acetate
  5. customto isolate the pure product in crystalline form
  6. additionTo the remainder of the reaction mixture is added 100 ml
  7. stirringwith stirring
  8. temperaturechilling
  9. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-f3b8fbc6e3324413adc8e2b034d1fe22
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011319

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