Water → 1-(4-Bromophenyl)-4-(methylsulfonyl)piperazine

HRID 40694Notes

Reaction equation

HRID 40694 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27356291-(4-Bromophenyl)piperazine

Product 1

HCID 219193841-(4-Bromophenyl)-4-(methylsulfonyl)piperazineYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Bromophenyl)piperazine (5 g, 20.7 mmol) is placed in 104 ml of dichloromethane and then triethylamine (4.34 ml, 31.1 mmol) is added, followed, dropwise, by methanesulfonyl chloride (1.93 ml, 24.9 mmol). Stirring is maintained for 16 h. After the addition of 30 ml of water and stirring, the organic phase is washed with a saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated. 6.6 g of expected 1-(4-bromophenyl)-4-methanesulfonylpiperazine are obtained.

Workup

  1. temperatureis maintained for 16 h
  2. stirringstirring
  3. washthe organic phase is washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb724b676d6c4ddc89c7c0ee5d97c752
Source dataset
uspto-grants-2013_09
Patent number
US08530477B2

Reaction notes

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