4-Chlorostyrene oxide → N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine

HRID 596623Notes

Reaction equation

HRID 596623 reaction equation
[CH2:1]([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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([CH:26]2[O:28][CH2:27]2)=[CH:24][CH:23]=1>CO>[CH2:1]([N:8]([CH2:27][CH:26]([OH:28])[C:25]1[CH:29]=[CH:30][C:22]([Cl:21])=[CH:23][CH:24]=1)[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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1970104-Chlorostyrene oxideHCID 200274Benzyl-[2-(3,4-dimethoxy-phenyl)-ethyl]-amine

Product 1

HCID 21450201N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Similarly 5.42 g. (0.02 mol) of N-benzyl-3,4-dimethoxyphenethylamine and 4.64 g. (0.03 mol) of p-chlorostyrene oxide are reacted in methanol to give N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine. The hydrochloride of this ethylamine is dissolved in methanol and hydrogenated with 0.5 g. of 10% palladium-on-carbon in 10 ml. of ethyl acetate at room temperature and 60 psi. for about 90 minutes. The filtered reaction mixture is evaporated in vacuo to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(4-chlorophenyl)ethylamine hydrochloride, m.p. 167°-171° C.

Sources & evidence

ORD record
ord-75c61e31a26f4907b5664787bb8f72b0
Source dataset
uspto-grants-1977_03
Patent number
US04011319

Reaction notes

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