4-Fluorobenzenesulfonyl chloride → HCID 10270693, compound

HRID 1006425Notes

Reaction equation

HRID 1006425 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][NH:14]3)[CH2:6][CH2:5]1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1(C)C=CC=CC=1.O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:14]2[C:15]3[C:11](=[C:10]([N:7]4[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]4)[CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

7

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 226712684-(4-methyl-piperazin-1-yl)-1H-indole dihydrochloride

Product 1

HCID 10270693HCID 10270693, compoundYield 70.5%

Reagents, catalysts & solvents 4

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

Procedure

A mixture of 0.2 g (0.79 mmole) 4-(4-methyl-piperazin-1-yl)-1H-indole dihydrochloride, 0.2 g (1.03 mmole) 4-fluorobenzenesulfonyl chloride and 0.025 g tetrabutylammonium hydrogen sulfate in 5 mL 4M sodium hydroxide and 15 mL toluene was stirred at room temperature for 24 hrs. The mixture was diluted with 10 mL water and extracted with 25 mL ethyl acetate. The organic phase was washed with 5 mL water, 5 mL saturated sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure. The hydrochloride salt was recrystallized from ethyl acetate/ether to provide 0.208 g of 1-(4-fluoro-benzenesulfonyl)-4-(4-methyl-piperazin-1-yl)-1H-indole (32), m.p. 151-152° C.

Workup

  1. extractionextracted with 25 mL ethyl acetate
  2. washThe organic phase was washed with 5 mL water, 5 mL saturated sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe hydrochloride salt was recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-46bf51519d04499c8a79d97b61e5abe5
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Reaction notes

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