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

HRID 596619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596619
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3ae100cd7f184af2a778326758db8ffc
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011319

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