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

HRID 596616Notes

Reaction equation

HRID 596616 reaction equation
[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][CH:22]=[CH:21][C:17]=1[CH:18]1[O:20][CH2:19]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:19][CH:18]([OH:20])[C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[O:15][CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 8421HomoveratrylamineHCID 113555722-(2-Methoxyphenyl)oxirane

Product 1

HCID 20434091N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methoxyphenyl)ethylamine

Procedure

A mixture of 33,5 g. (0.185 mol) of 3,4-dimethoxyphenylethylamine and 28 g. of o-methoxystyrene oxide is heated with stirring under argon on a steam bath overnight. A sample is chromatographed to obtain a pure sample of the product. This pure seed and 200 ml. of 2:1 ethyl acetatepetroleum ether are added to the reaction mixture. Chilling and stirring yields the product N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methoxyphenyl)ethylamine. m.p. 88° C.

Workup

  1. additionA mixture of 33,5 g
  2. customA sample is chromatographed
  3. customto obtain a pure sample of the product
  4. additionof 2:1 ethyl acetatepetroleum ether are added to the reaction mixture
  5. temperatureChilling
  6. stirringstirring

Sources & evidence

ORD record
ord-a3adeb3c9c434fe3821b40b575228d27
Source dataset
uspto-grants-1977_03
Patent number
US04011319

Reaction notes

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