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

HRID 427053

反応式

HRID 427053 の反応式
[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]

参加物

4

反応物 2

HCID 8421HomoveratrylamineHCID 980482-(4-Methoxyphenyl)oxirane

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226206Ethyl acetate hexane溶媒

実験手順

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 A sample is withdrawn from the reaction mixture and chromatographed on a silica column, eluting with benzene ethyl acetate to isolate the pure product in crystalline form.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

後処理

  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 customA sample is withdrawn from the reaction mixture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

出典と根拠

ORDレコード
ord-68690ff064ef455e91c38588b8446292
出典データセット
uspto-grants-1979_10
特許番号
US04172890

関連ノート

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