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Sodium Hydroxide → 1-[(5-Chloroindol-2-yl)sulfonyl]-3-(ethyl)piperazine

HRID 352800
Notes
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Reaction equation

HRID 352800 reaction equation
[OH-].[Na+].O1CCOCC1.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15](S(C1C=CC=CC=1)(=O)=O)[C:14]([S:28]([N:31]1[CH2:36][CH2:35][NH:34][CH:33]([CH2:37][CH3:38])[CH2:32]1)(=[O:30])=[O:29])=[CH:13]2.[Cl-].[NH4+]>C(OCC)(=O)C.O>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([S:28]([N:31]1[CH2:36][CH2:35][NH:34][CH:33]([CH2:37][CH3:38])[CH2:32]1)(=[O:30])=[O:29])=[CH:13]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 312751,4-DioxaneHCID 22710634HCID 22710634, compound

Product 1

HCID 227098481-[(5-Chloroindol-2-yl)sulfonyl]-3-(ethyl)piperazine

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A 1N aqueous solution (16 ml) of sodium hydroxide was added to a 1,4-dioxane solution (200 ml) of 1-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-3-(ethyl)piperazine (3.78 g) and the resulting mixture was stirred at 80° C. for 11.5 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Distilled water and ethyl acetate were then added and the water layer was extracted three time. 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=1:100), followed by crystallization from tetrahydrofuran—diethyl ether, whereby the title compound (2.54 g) was obtained as needle crystals.

Workup

  1. extractionthe water layer was extracted three time
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customfollowed by crystallization from tetrahydrofuran—diethyl ether, whereby the title compound (2.54 g)
  6. customwas obtained as needle crystals

Sources & evidence

ORD record
ord-405cd9d5df7248f09349e6d88a6a9ea3
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes