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

HRID 2420085Notes

Reaction equation

HRID 2420085 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 27.1 g. (0.1 mole) of N-benzyl-3,4-dimethoxyphenylethylamine and 23.3 g. (0.15 mole) 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 mole) 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.

Workup

  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 mole) 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

Sources & evidence

ORD record
ord-8986ff14c96d46999b8276555cbeee1e
Source dataset
uspto-grants-1978_08
Patent number
US04108989

Reaction notes

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