Potassium Carbonate → HCID 21519187, compound

HRID 1754896Notes

Reaction equation

HRID 1754896 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1.O.Cl.[NH:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O>[Cl:7][C:8]1[CH:9]=[C:10]([S:14]([N:20]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 179093-Chlorobenzenesulphonyl chlorideHCID 516892Sodium BicarbonateHCID 2723901Piperonylamine

Product 1

HCID 21519187HCID 21519187, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Potassium carbonate (13.96 g, 101.1 mmol) and 3-chlorobenzenesulfonyl chloride were continuously added to a two-phase solution of 4-piperidone hydrochloride hydrate (6.06 g, 39.48 mmol) in chloroform (47.4 mL) and water (47.4 mL), and the mixture was stirred at room temperature. A saturated aqueous sodium bicarbonate solution was added, and the organic layer and the aqueous layer were separated. The aqueous layer was then further extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting solid was washed with n-hexane and then collected by filtration and dried under reduced pressure to give 1-(3-chloro-benzenesulfonyl)-piperidin-4-one as a white solid (10.5 g, 97%).

Workup

  1. customthe organic layer and the aqueous layer were separated
  2. extractionThe aqueous layer was then further extracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting solid was washed with n-hexane
  6. filtrationcollected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-b2a8a1c12b154936a9accdbb7a134f55
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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