Piperidine → 1-(4-Fluorophenylsulfonyl)piperidine

HRID 1634836Notes

Reaction equation

HRID 1634836 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[F:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C1COCC1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 7553751-(4-Fluorophenylsulfonyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of piperidine (5.64 g, 66 mmol), diisopropylethyl amine (1 3.64 mL, 78 mmol), and p-fluorobenzenesulfonyl chloride (13.64 mL, 78 mmol) in THF at 0° C. was stirred for 2 hours at ambient temperature. The solvent was removed in vacuo and the crude reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with aqueous HCl, and brine. It was dried over sodium sulfate, and filtered. Removal of the solvent gave near quantitative yield of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with aqueous HCl, and brine
  5. dry with materialIt was dried over sodium sulfate
  6. filtrationfiltered
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-079b12a48d7c410c932b2a438f8babd6
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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