HCID 22625653, compound → HCID 10133212, compound

HRID 1738901Notes

Reaction equation

HRID 1738901 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:20](=[O:36])[CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)(=O)=O)C=CC=CC=1>CO.[OH-].[Na+]>[NH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11]([C:20](=[O:36])[CH2:21][CH2:22][CH:23]1[CH2:24][CH2:25][N:26]([CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:27][CH2:28]1)=[CH:12]2

Participants

4

Reactant 1

HCID 22625653HCID 22625653, compound

Product 1

HCID 10133212HCID 10133212, compoundYield 124.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(1-Phenylsulfonyl-5-amino-indol-2-yl)-3-(N-phenylmethylpiperidin-4-yl)-1-propanone (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 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-cb1ab0aa325b4f07b85fdb547fc1f063
Source dataset
uspto-grants-1999_10
Patent number
US05965574

Reaction notes

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