HCID 15549621, compound → HCID 15872237, compound

HRID 1899872Notes

Reaction equation

HRID 1899872 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-ae49d0d0b3ec46009c3ee0b3359ea1de
Source dataset
uspto-grants-1996_11
Patent number
US05574046

Reaction notes

Loading…