2-BroMostyrene oxide → HCID 20518157, compound

HRID 223109Notes

Reaction equation

HRID 223109 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])[C:12]=1[Cl:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[CH:25]1[O:27][CH2:26]1>CO>[CH2:1]([N:8]([CH2:26][CH:25]([OH:27])[C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[Br:22])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=1[Cl:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 110308142-BroMostyrene oxideHCID 20518142HCID 20518142, compound

Product 1

HCID 20518157HCID 20518157, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Similarly 2.71 g of N-benzyl-2-chloro-3,4-dimethoxyphenethylamine and 2.33 g (0.015 mol) of o-bromostyrene oxide are reacted in methanol to give N-benzyl-N-[2-(2-chloro-3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-bromophenyl)ethylamine. The latter is converted to its hydrochloride, which is dissolved in 90 ml of methanol and hydrogenated over 1 g of 10% palladium-on-carbon in 10 ml of ethyl acetate at room temperature for six hours. The reaction mixture is filtered and evaporated in vacuo to leave N-[2-(2-chloro-3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-bromophenyl)ethylamine hydrochloride.

Sources & evidence

ORD record
ord-b1e7d2539cdf495ebbaa7dfbad420b3e
Source dataset
uspto-grants-1982_10
Patent number
US04352754

Reaction notes

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