p-Bromobenzenesulfonyl chloride → 1-(4-Bromophenylsulfonyl)-4-methylpiperazine
Reaction equation
CN1CCOCC1.[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:12]2[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-methylmorpholine (60 g, 65 mL, 0.6 mol) is dissolved in DCM (100 mL), to which 1-methylpiperazine (30.5 g, 0.3 mol) is added. The reaction is cooled to 0° C., after which a solution of 4-bromo-benzenesulfonyl chloride (75.8 g, 0.296 mol) in DCM (100 mL) is added dropwise. The reaction is allowed to warm to RT overnight. The reaction mixture is then concentrated and water (1 L) is added. The solids that are formed are filtered and the filtrate is extracted with EtOAc (500 mL). The organic layer is washed with saturated brine, dried over MgSO4, filtered and concentrated to afford 1-(4-bromo-benzenesulfonyl)-4-methyl-piperazine as a pale yellow solid: LC/MS 321.0 (M+1); 1H NMR (400 MHz, CDCl3) δ 2.3 (s, 3 H) 2.5 (m, 4 H) 3.0 (m, 4 H) 7.6 (dt, J=8.8, 2.0 Hz, 2 H) 7.7 (dt, J=8.8, 2.1 Hz, 2 H).
Workup
- additionis added
- temperatureto warm to RT overnight
- concentrationThe reaction mixture is then concentrated
- additionwater (1 L) is added
- customThe solids that are formed
- filtrationare filtered
- extractionthe filtrate is extracted with EtOAc (500 mL)
- washThe organic layer is washed with saturated brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9c2f728116cb4fb38e8b816ed657b663
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795257B2
Reaction notes
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