82572-04-1

4657-12-9

163831-65-0

GENERAL METHOD: (R)-1-(1-naphthalenyl)ethylamine hydrochloride (1 mmol) was dissolved in methanol (10 mL), and benzaldehyde sodium bisulfite adduct (1.12 mmol) was added. Sodium cyanoborohydride (NaCNBH3, 2.5 mmol) was slowly added to the resulting suspension and the reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, the solvent was removed by evaporation to obtain the residue. The residue was partitioned with 5N NaOH solution and ethyl acetate (EtOAc). The aqueous phase was further extracted with EtOAc and the organic phases were combined, dried over anhydrous sodium sulfate and the solvent was evaporated to give the crude product. The crude product was dissolved in ether (Et2O) and treated with 0.6N ether-HCl solution. The resulting suspension was cooled at 0°C for 13 h. The precipitated white solid was collected by filtration and dried in vacuum to afford the target product (R)-N-benzyl-1-(naphthalen-1-yl)ethanamine hydrochloride.