1-[(5-Chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine → (5-Chloroindol-2-yl)sulfonyl-3-(2-methylpropyl)piperazine

HRID 352806Notes

Reaction equation

HRID 352806 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](S(C1C=CC=CC=1)(=O)=O)[C:6]([S:20]([N:23]1[CH2:28][CH2:27][NH:26][CH:25]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:24]1)(=[O:22])=[O:21])=[CH:5]2>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([S:20]([N:23]1[CH2:28][CH2:27][NH:26][CH:25]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:24]1)(=[O:22])=[O:21])=[CH:5]2

Participants

3

Reactant 1

HCID 227110221-[(5-Chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine

Product 1

HCID 22710654(5-Chloroindol-2-yl)sulfonyl-3-(2-methylpropyl)piperazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine (2.57 g) in a mixture of 1,4-dioxane and distilled water (100-10 ml) was added a 1N aqueous solution (10.4 ml) of sodium hydroxide. The resulting mixture was stirred at 80° C. for 3 days. After saturated ammonium chloride was added to terminate the reaction, distilled water and ethyl acetate were added. The water layer was extracted three times. The organic layers were combined, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:50), whereby the title compound (0.93 g) was obtained as a brown oil.

Workup

  1. distillationdistilled water (100-10 ml)
  2. additionwas added a 1N aqueous solution (10.4 ml) of sodium hydroxide
  3. additionAfter saturated ammonium chloride was added
  4. customto terminate
  5. customthe reaction
  6. distillationdistilled water and ethyl acetate
  7. additionwere added
  8. extractionThe water layer was extracted three times
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent
  12. customwas obtained as a brown oil

Sources & evidence

ORD record
ord-50f09e0695bb4a8e966c0ec1b61eb907
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…