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

HRID 596613

반응식

HRID 596613 반응식
[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]

참가 물질

4

반응물 2

HCID 8421HomoveratrylamineHCID 980482-(4-Methoxyphenyl)oxirane

생성물 1

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

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

실험 절차

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 A sample is withdrawn from the reaction mixture and chromatographed on a silica column, eluting with benzene ethyl acetate to isolate the pure product in crystalline form.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.

후처리

  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 customA sample is withdrawn from the reaction mixture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

출처 및 근거

ORD 기록
ord-f3b8fbc6e3324413adc8e2b034d1fe22
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04011319

연결된 노트

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