Potassium Hydroxide → HCID 10425204, compound

HRID 725968Notes

Reaction equation

HRID 725968 reaction equation
[OH-].[K+].[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)(=[O:6])=[O:5].[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1>CO>[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH:20]=1)(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 10036020HCID 10036020, compound

Product 1

HCID 10425204HCID 10425204, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.2 gm (21.4 mMol) potassium hydroxide in 12 mL methanol was added 1.0 gm (4.76 mMol) 5-methanesulfonylamino-1H-indole followed by 0.76 mL (6.2 mMol) 1-methyl-4-piperidone. The homogeneous solution was heated to reflux for 18 hours under nitrogen. The reaction mixture was then cooled and concentrated under reduced pressure. The residue was dissolved in water and the pH of the solution adjusted from 14 to 8-9 by the addition of acid. The precipitate that formed was filtered, washed with water and dried under vacuum to give 1.3 gm (89.6%) of the title compound as a tan solid.

Workup

  1. temperatureThe homogeneous solution was heated
  2. temperatureto reflux for 18 hours under nitrogen
  3. temperatureThe reaction mixture was then cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. additionthe pH of the solution adjusted from 14 to 8-9 by the addition of acid
  7. customThe precipitate that formed
  8. filtrationwas filtered
  9. washwashed with water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-7707a8d96df04103a8ff7e6c9d06a595
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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