[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[CH3:17][O:18][CH:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH2:20][NH2:21].C(OCC)(=O)C>C1(C)C=CC=CC=1>[ClH:28].[ClH:28].[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:21][CH2:20][CH:19]([O:18][CH3:17])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2]1-(4-carbomethoxymethoxyphenyl)propan-2-one (2.80 g) and 2-methoxy-2-(3-chlorophenyl)ethanamine (2.58 g) in dry toluene (200 ml) were boiled under reflux for 2 hours in an apparatus incorporating a water trap. The solution was cooled and the solvent removed under reduced pressure. The residue dissolved in methanol (100 ml) was hydrogenated in the presence of platinum (from platinum oxide, 50 mg) until hydrogen uptake ceased. The solution was filtered through diatomaceous earth, and the solvent removed under reduced pressure. Chromatography of the residue on silica-gel in 3% methanol-dichloromethane gave an oil. Treatment of this oil with an ethereal solution of hydrogen chloride gave N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine hydrochloride, mp 148°-50° C. (ethyl acetate), as an 85:15 mixture of diastereoisomers.
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