Dimethyl Sulfoxide → 1-(3-Chloropyridin-2-yl)piperidin-4-one

HRID 404565Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

At −78° C., DMSO (10 g, 138 mmol) was added slowly into a dichloromethane (40 ml) solution of oxalyl dichloride. After 15 minutes, N-(3-chloro-2-pyridyl)-4-hydroxy piperidine (compound 20) in methylene chloride was added dropwise into the reaction mixture. After 30 minutes, 31 g of triethylamine was slowly added, when the reaction solution was maintained at −78° C. Reaction mixture was slowly warmed to room temperature. Three times of water was added into the reaction solution. The reaction mixture was extracted by ethyl acetate. The organic layer was evaporated to give a crude product, which was purified using column chromatography to give the product. (13 g, 93%)

Workup

waitAfter 30 minutes
customReaction mixture
temperaturewas slowly warmed to room temperature
extractionThe reaction mixture was extracted by ethyl acetate
customThe organic layer was evaporated

Sources & evidence

ORD record: ord-0436433f586e40bbad73b64f73b3b5ef
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748610B2

Reaction notes

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