Triethylamine → 1-[(5-Bromo-2-thienyl)sulfonyl]-4-(4-fluorophenyl)piperazine
Reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([S:7]([N:28]2[CH2:27][CH2:26][N:25]([C:22]3[CH:21]=[CH:20][C:19]([F:18])=[CH:24][CH:23]=3)[CH2:30][CH2:29]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (5-bromo(2-thienyl))chlorosulfone (1.09 g, 4.16 mmol) in CH2Cl2 (30 mL) was added triethylamine (0.4 mL, 3.052 mmol), followed by (4-fluorophenyl)piperazine (500 mg, 2.77 mmol). The resulting mixture was stirred at room temperature overnight. The reaction was treated with a saturated NaHCO3 solution (1 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with a saturated NaCl solution (10 mL), dried (MgSO4) and concentrated under reduced pressure to give a brown solid. The crude product was purified flash chromatography (10% EtOAc/hex) to give 5-bromo-2-{[4-(4-fluorophenyl)piperazinyl]sulfonyl}thiophene (1.12 g, 100%) as a white solid: mp 123-124° C.; TLC (EtOAc) Rf 0.44; HPLC ES-MS m/z 406 (MH+).
Workup
- extractionextracted with EtOAc (3×10 mL)
- washThe combined organic layers were washed with a saturated NaCl solution (10 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- customto give a brown solid
- customThe crude product was purified flash chromatography (10% EtOAc/hex)
Sources & evidence
- ORD record
- ord-6be2af50650d4a14baa7270c30f384f3
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06784167B2
Reaction notes
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