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

HRID 427053

반응식

HRID 427053 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 mmole) of 3,4-dimethyloxyphenylethylamine and 13.5 g. (88 mmole) 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 A sample is withdrawn from the reaction mixture and chromatographed on a silica column, eluting with benzene ethyl acetate to isolate the pure product in crystalline form.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 customA sample is withdrawn from the reaction mixture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-68690ff064ef455e91c38588b8446292
출처 데이터셋
uspto-grants-1979_10
특허 번호
US04172890

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