O=[CH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1.Cl.[CH3:16][NH:17][CH3:18].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO>[CH3:16][N:17]([CH3:18])[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1To a suspension of N-[4-(3-Oxo-propyl)-phenyl]-acetamide (96 mg, 0.50 mmol), dimethylamine hydrochloride (82 mg, 1.0 mmol), and sodium acetate (66 mg, 0.80 mmol) in methanol (0.5 mL) is added sodium cyanoborohydride (47 mg, 0.75 mmol). Upon completion of the reaction, the solvent is evaporated under reduced pressure and the residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate. The combined extracts were concentrated to give N-[4-(3-dimethylamino-propyl)-phenyl]-acetamide (0.14 g, >100%).
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