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

HRID 272952Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([C:23]#[N:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C(OCC)C.CO.ClCCl>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([CH2:23][NH2:24])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-8112c4305d5b4f2d940ba43ab719bb31
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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