Potassium Carbonate → (1-Benzhydrylpiperidin-4-yl)methanol

HRID 1849883Notes

Reaction equation

Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:2]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (bromomethylene)dibenzene (115 mg, 1.0 mmol) and piperidin-4-ylmethanol (247 mg, 1.0 mmol) in DMF (5 mL) was added potassium carbonate (276 mg, 2.0 mmol), and the reaction mixture was stirred at 100° C. for 16 h. After cooling to room temperature, the mixture was quenched with water (50 mL) and extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica column chromatography (eluting with petroleum ether/ethyl acetate=3/1) to give (1-benzhydrylpiperidin-4-yl)methanol (280 mg, 99% yield) as white solid. LCMS (ESI) m/z: 281.9 [M+H]+.

Workup

temperatureAfter cooling to room temperature
customthe mixture was quenched with water (50 mL)
extractionextracted with ethyl acetate (10 mL×3)
washThe combined organic layers were washed with brine (20 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica column chromatography (eluting with petroleum ether/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-1e92c839fb60434b8ee1edfe330db0b8
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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