3,5-Dichlorobenzenesulfonyl chloride → 4-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole

HRID 1006417

Reaction equation

HRID 1006417 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([S:31](Cl)(=[O:33])=[O:32])[CH:27]=[C:28]([Cl:30])[CH:29]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+].O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[S:31]([C:26]2[CH:25]=[C:24]([Cl:23])[CH:29]=[C:28]([Cl:30])[CH:27]=2)(=[O:33])=[O:32])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 27285324-(4-Benzyl-piperazin-1-yl)-1H-indole

Product 1

HCID 121371244-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indoleYield 100.5%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-(4-Benzyl-piperazin-1-yl)-1H-indole (274 mg, 0.94 mmole) and 50 mg tetra-n-butylammonium hydrogen sulfate was stirred in a mixture of 10 mL toluene and 5 mL 4 N sodium hydroxide. Solid 3,5-dichlorobenzenesulfonyl chloride (246 mg, 1.0 mmole) was added in one portion. The reaction mixture was stirred at room temperature for 6 hours, then it was diluted with 20 mL water and extracted with 25 mL ethyl acetate. The organic phase was washed with 10 mL saturated sodium chloride solution, dried (magnesium sulfate) and concentrated. Recrystallization from dichloromethane provided 473 mg of 4-(4-benzyl-piperazin-1-yl)-1-(3,5-dichloro-benzenesulfonyl)-1H-indole, m.p. 201-203° C.

Workup

  1. extractionextracted with 25 mL ethyl acetate
  2. washThe organic phase was washed with 10 mL saturated sodium chloride solution
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customRecrystallization from dichloromethane

Sources & evidence

ORD record
ord-9c0ec165595848a990ab93ee514ccaec
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Linked notes

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