p-Bromobenzenesulfonyl chloride → 1-(4-Bromophenylsulfonyl)-4-methylpiperazine

HRID 1879901Notes

Reaction equation

HRID 1879901 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 531671-MethylpiperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 7107291-(4-Bromophenylsulfonyl)-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromobenzene-1-sulfonyl chloride (256 mg, 1.00 mmol) in 1 mL of dichloromethane was slowly added to a vial (40 mL) containing 5 mL of a saturated aqueous solution of sodium bicarbonate, dichloromethane (5 mL) and 1-methylpiperazine (100 mg, 1.00 mmol). The reaction was stirred at room temperature overnight. The phases were separated and the organic layer was dried over magnesium sulfate. Evaporation of the solvent under reduced pressure provided the required product, which was used in the next step without further purification. ESI-MS m/z calc. 318.0, found 318.9 (M+1)+. Retention time of 1.30 minutes. 1H NMR (300 MHz, CDCl3) δ 7.65 (d, J=8.7 Hz, 2H), 7.58 (d, J=8.7 Hz, 2H), 3.03 (t, J=4.2 Hz, 4H), 2.48 (t, J=4.2 Hz, 4H), 2.26 (s, 3H).

Workup

  1. customThe phases were separated
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a58ba50e96304534a6c177a386d083df
Source dataset
uspto-grants-2012_11
Patent number
US08318733B2

Reaction notes

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