4-Fluorobenzenesulfonyl chloride → 1-((4-Fluorophenyl)sulfonyl)-4-methylpiperazine

HRID 1964699Notes

Reaction equation

HRID 1964699 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 7679141-((4-Fluorophenyl)sulfonyl)-4-methylpiperazineYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Commercially available 4-fluorobenzenesulfonyl chloride (1.00 g, 5.14 mmol) was suspended in water (15 mL), and N-methylpiperazine (0.68 mL, 6.17 mmol) and potassium carbonate (1.56 g, 11.3 mmol) were added, followed by stirring at room temperature for 14 hours under nitrogen atmosphere. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL), and subsequently the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-90%) to afford the desired compound (491 mg, yield 37%) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 mL)
  2. washsubsequently the organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-90%)

Sources & evidence

ORD record
ord-e1ab29b40b624dad829448dbc6e65db4
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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