Sodium Carbonate → 1-{[3-(Chloromethyl)phenyl]sulfonyl}piperidine

HRID 1967558Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=O.[N:6]1([S:12]([C:15]2[CH:16]=[C:17]([CH2:21]O)[CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:3][CH2:21][C:17]1[CH:16]=[C:15]([S:12]([N:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Phosphorus oxychloride (1.00 mL) was added to DMF (5.0 mL), and stirred at 80° C. for 30 minutes. A solution prepared by dissolving [3-(piperidin-1-ylsulfonyl)phenyl]methanol (2.00 g) obtained in Reference Example 21 in DMF (5.0 mL) was added to it, and stirred at 80° C. for 30 minutes. At 0° C., aqueous saturated sodium carbonate solution was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient) to give the entitled compound (1.26 g, 59%) as a colorless solid.

Workup

customA solution prepared
additionwas added to it
stirringstirred at 80° C. for 30 minutes
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine in that order
dry with materialdried with sodium sulfate
customThe drying agent was removed through filtration
customthe solvent was evaporated off under reduced pressure
customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient)

Sources & evidence

ORD record: ord-944b10a56b32427ca3664bb1a5e99fd7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420823B2

Reaction notes

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