Water → (4-{4-[(1-isopropylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methylamine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 4-[4-(1-isopropylpiperidin-4-yloxy)phenyl]tetrahydropyran-4-carbonitrile (2.5 g, 7.62 mmol) in dry diethyl ether (15 ml) at 0° C. was added dropwise a solution of LiAlH4 (1.0M solution in Et2O, 22.87 ml, 22.9 mmol). Reaction stirred at 0° C. for 30 min, then warmed up to ambient temperature overnight under a nitrogen atmosphere until complete. The reaction was cooled to 0° C., water (0.9 ml) was added dropwise followed by sodium hydroxide (2.0M, 0.9 ml) and water (2.7 ml). Dichloromethane (25 ml) and methanol (1 ml) were added and the mixture filtered through a short pad of arbocel, eluting with 2% methanol in dichloromethane (200 ml). The organic washings were dried over Na2SO4 and concentrated in vacuo to give the title compound as an orange oil (2.59 g, 100%).

Provenance & Evidence