solution was added hcl saturated ether the resulting mixture was filtered to afford 1 2 g enantiomerically homogeneous cis 3 2 methoxybenzyl amino 2 phenylpiperidine hydrochloride as a white solid u03b1 d 79 5 u00b0 meoh c 0 98 1 under a nitrogen atmosphere in a round bottom flask were placed 500 mg 2 9 mmol of 2 phenyl 3 aminopyridine 10 ml of methanol and 1 g of 3a molecular sieves the ph of the system was adjusted to ca 4 5 using methanol saturated with hcl and 190 mg 2 9 mmol of sodium cyanoborohydride was added to the system the ph of the system was adjusted to 4 5 474 mg 3 5 mmol of 2 methoxybenzaldehyde was added and the mixture was stirred at room temperature overnight the mixture was filtered through celite u00ae and the filtrate was concentrated the residue was partitioned between ch 2 cl 2 and saturated aqueous sodium bicarbonate the layers were separated and the aqueous phase was extracted with three portions of ch 2 cl 2 the combined organic fractions were dried na 2 so 4 and concentrated with a rotary evaporator the crude material was purified by flash column chromatography to obtain 475 mg of 3 2 methoxybenzylamino 2 phenylpyridine mp 128 u00b0 129 u00b0 c 1 h nmr cdcl 3 u03b4 7 60 d 1h j 6.