Water → HCID 44549020, compound

HRID 560127Notes

Reaction equation

HRID 560127 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]3[CH2:23][NH:22][CH2:21][CH2:20][N:19]3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O.C(OCC)(=O)C>C1COCC1>[C:31]1([S:37]([N:22]2[CH2:21][CH2:20][N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])[CH:18]([C:14]3[CH:13]=[C:12]([C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=4)[CH:17]=[CH:16][CH:15]=3)[CH2:23]2)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 67001255HCID 67001255, compound

Product 1

HCID 44549020HCID 44549020, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3′-methanesulfonyl-biphenyl-3-yl)-1-o-tolyl-piperazine hydrochloride (58 mg) in THF (1 mL) sodium hydride (12.3 mg, 60% in mineral oil) was added. After stirring for 30 min at room temperature, benzenesulfonyl chloride was added at 0° C. and stirring was continued at room temperature overnight. Water and ethyl acetate was added, the phases were separated and the inorganic one was extracted with ethyl acetate (×3). The combined organic layers were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, n-heptane/ethyl acetate 2:1,) yielded 4-benzenesulfonyl-2-(3′-methanesulfonyl-biphenyl-3-yl)-1-o-tolyl-piperazine (55 mg, 42%) as colorless oil, MS: 547.1 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customthe phases were separated
  4. extractionthe inorganic one was extracted with ethyl acetate (×3)
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6612eee7ba14ef9847a9b1d6c454c76
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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