Piperazine → 5-Fluoro-1-(4-piperazin-1-yl-benzenesulfonyl)-1H-indole

HRID 1793869Notes

Reaction equation

HRID 1793869 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CS(C)=O.O>[F:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:12]=[CH:13]2

Participants

5

Reactant 2

HCID 4837PiperazineHCID 222201261-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole

Product 1

HCID 99985735-Fluoro-1-(4-piperazin-1-yl-benzenesulfonyl)-1H-indoleYield 48.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 1-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole (0.210 g, 0.7 mmole) and anhydrous piperazine (0.3 g, 3.4 mmole) in dimethylsulfoxide (3.0 mL) was heated at 100° in a sealed tube for 16 h. The reaction mixture was diluted with 15 mL water and extracted with 20 mL ethyl acetate. The organic phase was washed with three 10 mL portions of water, 10 mL saturated sodium chloride, dried (magnesium sulfate), and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to provide the 5-Fluoro-1-(4-piperazin-1-yl-benzenesulfonyl)-1H-indole (0.123 g), m.p. 77–78°.

Workup

  1. extractionextracted with 20 mL ethyl acetate
  2. washThe organic phase was washed with three 10 mL portions of water, 10 mL saturated sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-149316315f5344be8e5c9550c7eb59e8
Source dataset
uspto-grants-2006_04
Patent number
US07022708B2

Reaction notes

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