2-(3-Chlorophenyl)oxirane → N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(3-chlorophenyl)ethylamine hydrochloride

HRID 596619ノート

反応式

HRID 596619 の反応式
C([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)C1C=CC=CC=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[CH:25]1[O:27][CH2:26]1>CO>[ClH:21].[CH3:20][O:19][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][NH:8][CH2:26][CH:25]([OH:27])[C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=2)[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

参加物

4

反応物 2

HCID 1556132-(3-Chlorophenyl)oxiraneHCID 200274Benzyl-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

生成物 1

HCID 20387913N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(3-chlorophenyl)ethylamine hydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 27.1 g. (0.1 mol) of N-benzyl-3,4-dimethoxyphenylethylamine and 23.3 g. (0.15 mol) of m-chlorostyrene oxide in 500 ml. of methanol is stirred and refluxed overnight. The methanol is removed in vacuo and the residual N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(3-chlorophenyl)ethylamine is reduced without further purification. This sample (0.01 mol) is dissolved in ether, acidified with ethereal hydrogen chloride and hydrochloride precipitates. The latter is dissolved in 90 ml. of methanol, the solution is added to a mixture of 0.5 g. of palladium-on-carbon in 10 ml. of ethyl acetate and the mixture is hydrogenated at room temperature for 90 minutes at 60 psi. The reaction mixture is filtered and the filtrate evaporated in vacuo to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(3-chlorophenyl)ethylamine hydrochloride, m.p. 155°-157.5° C.

後処理

  1. temperaturerefluxed overnight
  2. customThe methanol is removed in vacuo
  3. customthe residual N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(3-chlorophenyl)ethylamine is reduced without further purification
  4. dissolutionThis sample (0.01 mol) is dissolved in ether
  5. customprecipitates
  6. dissolutionThe latter is dissolved in 90 ml
  7. additionof methanol, the solution is added to a mixture of 0.5 g
  8. filtrationThe reaction mixture is filtered
  9. customthe filtrate evaporated in vacuo

出典と根拠

ORDレコード
ord-3ae100cd7f184af2a778326758db8ffc
出典データセット
uspto-grants-1977_03
特許番号
US04011319

反応ノート

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