HCID 15549621, compound → HCID 15872237, compound

HRID 380636Notes

Reaction equation

HRID 380636 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([C:18]3[N:19](S(C4C=CC=CC=4)(=O)=O)[C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][CH:21]=4)=[O:17])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[OH-].[Na+]>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][CH:21]=4)=[O:17])[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 15549621HCID 15549621, compound

Product 1

HCID 15872237HCID 15872237, compoundYield 115%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-phenylsulfonyl-5-nitroindol-2-yl 2-[1-(phenylmethyl)-4-piperidinyl]ethyl ketone (160 mg, 0.32 mmol) in 3 ml of methanol and 2 ml of 2N NaOH was heated at reflux for 2 hours. The mixture was concentrated to dryness and the residue was diluted with brine and extracted with chloroform. The organic layer was dried and concentrated to dryness to give 144 mg of a brown solid which was purified through silica gel column chromatography to give 31 mg of the title compound as a brown solid.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe mixture was concentrated to dryness
  3. additionthe residue was diluted with brine
  4. extractionextracted with chloroform
  5. customThe organic layer was dried
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6272316bac2843c88dafae4158b5c3b0
Source dataset
uspto-grants-2001_10
Patent number
US06303633B1

Reaction notes

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