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

HRID 352800Notes

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

Participants

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

extractionthe water layer was extracted three time
dry with materialdried over anhydrous magnesium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customfollowed by crystallization from tetrahydrofuran—diethyl ether, whereby the title compound (2.54 g)
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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