Water → (2-Oxo-1-phenylpiperidin-4-yl)methyl methanesulfonate

HRID 341051Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[CH2:4]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>ClCCl>[CH3:23][S:24]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[CH2:4]1)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(Hydroxymethyl)-1-phenylpiperidin-2-one (0.27 g, 1.3 mmol) was dissolved in dichloromethane (15 mL), cooled to 0° C. and treated with triethylamine (1.0 mL, 7.2 mmol, 5.5 equiv). To the mixture was added methanesulfonyl chloride (0.10 mL, 1.3 mmol, 1 equiv), the mixture was warmed to ambient temperature and stirred for an additional 15 hours. The mixture was poured into water (25 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

temperaturethe mixture was warmed to ambient temperature
extractionextracted with dichloromethane (2×20 mL)
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-78f78218f2f74335aee45edbbba99cab
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895580B2

Reaction notes

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