Potassium Hydroxide → HCID 23513734, compound

HRID 352913Notes

Reaction equation

HRID 352913 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=3)[CH:12]=[C:11]2[S:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:42])[C:30]3[CH:35]=[CH:34][C:33]([C:36]4[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=4)=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)(=[O:22])=[O:21])(=O)=O)C=CC=CC=1.[OH-].[K+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O1CCCC1.ClCCl.CO>[Cl:19][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[C:11]([S:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:42])[C:30]4[CH:31]=[CH:32][C:33]([C:36]5[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=5)=[CH:34][CH:35]=4)[CH2:25][CH2:24]3)(=[O:22])=[O:21])[NH:10]2)=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 22711121HCID 22711121, compound

Product 1

HCID 23513734HCID 23513734, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (4.0 ml), 1-[(1-phenylsulfonyl-6-chloroindol-2-yl)sulfonyl]-4-[4-(pyridin-4-yl)benzoyl]piperazine (380 mg) was dissolved, followed by the addition of methanol (4.0 ml) and potassium hydroxide (34.3 mg) at room temperature. The resulting mixture was stirred for 2 hours. To the reaction mixture, a saturated aqueous solution (30 ml) of ammonium chloride was added to make it weakly acidic. Then, a saturated aqueous solution (40 ml) of sodium bicarbonate was added to make the resulting mixture to weakly alkaline. The resulting mixture was added with dichloromethane (30 ml). The organic layer thus separated was extracted further with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure. The residue thus obtained was purified by preparative thin-layer chromatography on a silica gel (dichloromethane:acetone:methanol=20:2:1), followed by recrystallization from a mixed solvent of hexane and dichloromethane, whereby the title compound (157 mg, 53%) was obtained as a white solid.

Workup

  1. customThe organic layer thus separated
  2. extractionwas extracted further with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by preparative thin-layer chromatography on a silica gel (dichloromethane:acetone:methanol=20:2:1)
  7. customfollowed by recrystallization from a mixed solvent of hexane and dichloromethane, whereby the title compound (157 mg, 53%)
  8. customwas obtained as a white solid

Sources & evidence

ORD record
ord-a246f4470117406d96e4c3bb74e7895a
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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