4-Fluorobenzenesulfonyl chloride → N-(1-acetylpiperidin-4-yl)-4-fluorobenzenesulfonamide

HRID 49781Notes

Reaction equation

HRID 49781 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)(=[O:4])[CH3:3].C(N(C(C)C)CC)(C)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][S:28]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 172216421-Acetyl-4-aminopiperidine hydrochloride

Product 1

HCID 9926350N-(1-acetylpiperidin-4-yl)-4-fluorobenzenesulfonamideYield 67,058.898%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 1-acetyl-4-aminopiperidine hydrochloride (715 mg) in dichloromethane (7 ml) were added diisopropylethylamine (1.83 ml) and a solution of 4-fluorobenzenesulfonyl chloride (0.83 mg) in dichloromethane (2 ml) at ambient temperature. After stirring for 6.5 hours, the reaction mixture was diluted with dichloromethane and washed with water, saturated aqueous sodium hydrogen carbonate, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. A residue was purified by column chromatography (silica gel 50 ml, dichloromethane:methanol=50:1 to 20:1). After rinse with diisopropyl ether, N-(1-acetylpiperidin-4-yl)-4-fluorobenzenesulfonamide (859 mg) was obtained.

Workup

  1. customat ambient temperature
  2. washwashed with water, saturated aqueous sodium hydrogen carbonate, and brine
  3. dry with materialAfter drying with magnesium sulfate
  4. customthe solvents were removed under reduced pressure
  5. customA residue was purified by column chromatography (silica gel 50 ml, dichloromethane:methanol=50:1 to 20:1)
  6. washAfter rinse with diisopropyl ether

Sources & evidence

ORD record
ord-9cbd0361abc743968418ad4fd839c0eb
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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