Water → 1-[(5-Chloroindol-2-yl)sulfonyl]piperazine hydrochloride

HRID 352772Notes

Reaction equation

HRID 352772 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[N:18](S(C3C=CC=CC=3)(=O)=O)[C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+].[Cl-].[NH4+].O>CO.ClCCl>[ClH:26].[Cl:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([S:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)(=[O:16])=[O:15])=[CH:25]2

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 227103001-tert-Butoxycarbonyl-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine

Product 1

HCID 227105701-[(5-Chloroindol-2-yl)sulfonyl]piperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In methanol (100 ml), 1-tert-butoxycarbonyl-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine (3.63 g) was dissolved. Under ice cooling, a 0.2N methanol solution of sodium hydroxide (100 ml) was added to the resulting solution, followed by stirring at room temperature for 12 hours. After a saturated aqueous solution of ammonium chloride was added to the reaction mixture under ice cooling, water and dichloromethane were added to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. After the solid so precipitated was collected by filtration, it was dissolved in saturated ethanol hydrochloride, followed by stirring for 30 minutes. The reaction mixture was distilled under reduced pressure to remove the solvent, followed by drying under reduced pressure, whereby the title compound (1.25 g, 54%) was obtained as colorless powder.

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customAfter the solid so precipitated
  5. filtrationwas collected by filtration, it
  6. dissolutionwas dissolved in saturated ethanol hydrochloride
  7. stirringby stirring for 30 minutes
  8. distillationThe reaction mixture was distilled under reduced pressure
  9. customto remove the solvent
  10. dry with materialby drying under reduced pressure, whereby the title compound (1.25 g, 54%)
  11. customwas obtained as colorless powder

Sources & evidence

ORD record
ord-2ceccd02ec31475194714ce350b7d926
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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