Water → 1-(3-Chloropyridin-2-yl)piperidin-4-ol

HRID 404564Notes

Reaction equation

HRID 404564 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]=1

Participants

5

Reactant 3

HCID 962WaterHCID 169882,3-DichloropyridineHCID 232933-Hydroxypiperidine2×

Product 1

HCID 607016561-(3-Chloropyridin-2-yl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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

  1. extractionThe reaction mixture was extracted by ethyl acetate
  2. 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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