Water → 1-(3-Chloropyridin-2-yl)piperidin-4-ol
Reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.O[CH:10]1[CH2:15][NH:14][CH2:13][CH2:12][CH2:11]1.[OH2:16]>CS(C)=O>[Cl:8][C:7]1[C:2]([N:14]2[CH2:13][CH2:12][CH:11]([OH:16])[CH2:10][CH2:15]2)=[N:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2,3-dichloropyridine (10 g, 68 mmol) and 5-hydroxyl piperidine (compound 19) (26 g, 272 mmol) in DMSO was heated at 120° C. and stirred overnight. After the reaction was completed, 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. (17 g, 93%)
Workup
- extractionThe reaction mixture was extracted by ethyl acetate
- customThe organic layer was evaporated
Sources & evidence
- ORD record
- ord-f815850a6cf4438fa49e999c908cfc72
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748610B2
Reaction notes
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