1-(3-Methoxyphenyl)acetone → N-[2-(3-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

HRID 1731578Notes

Reaction equation

HRID 1731578 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:7][CH:8]=1.[OH:13][CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[CH2:15][NH2:16]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([NH:16][CH2:15][CH:14]([OH:13])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH3:11])[CH:6]=[CH:7][CH:8]=1.[ClH:23].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([NH:16][CH2:15][CH:14]([OH:13])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH3:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 764101-(3-Methoxyphenyl)acetoneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-ol

Product 2

HCID 18628071N-[2-(3-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamineHCID 20228000N-[2-(3-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine hydrochloride

Procedure

N-[2-(3-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine was prepared from 1-(3-methoxyphenyl)propan-2-one (3.81 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (3.99 g) by an analogous procedure to that described in Example 1 and purified by column chromatography on silica gel using 2-5% methanol in dichloromethane as eluent. The purified amine was converted to its hydrochloride salt by addition of ethereal hydrogen chloride and crystallised from ethyl acetate-diethyl ether to give N-[2-(3-methoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine hydrochloride, m.p. 101°-4° C. as u a 60:40 mixture of diastereoisomers.

Workup

  1. custompurified by column chromatography on silica gel using 2-5% methanol in dichloromethane as eluent
  2. additionThe purified amine was converted to its hydrochloride salt by addition of ethereal hydrogen chloride
  3. customcrystallised from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-4d25c3e2e2614d2cb184974d0e6e39d8
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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