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

Temperature

0 °C

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%).

1. customReaction
2. temperaturewarmed up to ambient temperature overnight under a nitrogen atmosphere until complete
3. temperatureThe reaction was cooled to 0° C.
4. filtrationthe mixture filtered through a short pad of arbocel
5. washeluting with 2% methanol in dichloromethane (200 ml)
6. dry with materialThe organic washings were dried over Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-8112c4305d5b4f2d940ba43ab719bb31

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456164B2