[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[C:16]([OH:25])(=[O:24])[CH:17]([CH:19]([C:21]([OH:23])=[O:22])[OH:20])[OH:18]>O>[C:21]([CH:19]([CH:17]([C:16]([OH:25])=[O:24])[OH:18])[OH:20])([OH:23])=[O:22].[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1(3-Chlorophenyl)phenylmethylamine (9.25g, 42.5 mmol) and (−)-tartaric acid (7.02 g, 46.7 mmol) were dissolved in water (40 ml) with heating. Thereafter, the precipitated crude crystals obtained by allowing to cool the reaction solution to room temperature were collected by filtration. The resulting crystals were purified by repeatedly recrystallizing from water, to give (−)-(3-chlorophenyl)phenylmethylamine (−)-tartrate (4.58 g).
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