p-Bromobenzenesulfonyl chloride → HCID 1332328, compound

HRID 1644687Notes

Reaction equation

HRID 1644687 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O1CCCC1>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:18]2[CH2:19][CH2:20][N:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[F:8])[CH2:16][CH2:17]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 705291-(2-Fluorophenyl)piperazine

Product 1

HCID 1332328HCID 1332328, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.37 mL, 9.78 mmol) was added at 0° C. to a stirred solution of 1-(2-fluorophenyl)piperazine (0.705 g , 3.91 mmol) in tetrahydrofuran (12 mL) and the reaction mixture was stirred at room temperature for 15 minutes. 4-Bromo-benzenesulfonyl chloride (1.00 g, 3.91 mmol) was added to the reaction mixture at room temperature and the reaction mixture was stirred at room temperature for 5 hours. Tetrahydrofuran was evaporated off under reduced pressure. The residue was diluted with ethyl acetate (20 mL), and the inorganic salts were filtered through a celite bed. The filtrate was washed with 2.0 N aqueous HCl (8 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to provide 1.40 g (89%) of 1-(4-bromobenzenesulfonyl)-4-(2-fluoro-phenyl)piperazine as white solid. MS cald. for C16H16BrFN2O2S [M+] 399, obsd. 399.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 5 hours
  2. customTetrahydrofuran was evaporated off under reduced pressure
  3. additionThe residue was diluted with ethyl acetate (20 mL)
  4. filtrationthe inorganic salts were filtered through a celite bed
  5. washThe filtrate was washed with 2.0 N aqueous HCl (8 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d4634a26993499fb34e124ead65070b
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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