Potassium Hydroxide → HCID 22611373, compound

HRID 1738008Notes

Reaction equation

HRID 1738008 reaction equation
[OH-].[K+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([NH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)=[O:9].[CH2:20]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)C>CO>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([NH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:25]1[CH2:26][CH2:27][N:22]([CH3:20])[CH2:23][CH:24]=1)=[O:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 771591-Ethylpiperidin-4-oneHCID 22611244HCID 22611244, compound

Product 1

HCID 22611373HCID 22611373, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.868 gm (15.5 mMol) potassium hydroxide in 8 mL methanol were added 1.0 gm (4.42 mMol) 5-(2-furoyl)amino-1H-indole and 0.774 mL 1-ethyl-4-piperidone and the solution was stirred at reflux for 18 hours. The reaction mixture was cooled to ambient and then diluted with ice/water. The resultant precipitate was collected and dried under vacuum. This solid was purified by radial chromatography (2 mm silica), eluting with a gradient of dichloromethane containing 5-7.5% methanol and 0.5-1.0% ammonium hydroxide. The product was then crystallized from ethyl acetate to give 0.715 gm (48.3%) of the title compound as a bright yellow powder.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled to ambient and
  3. customThe resultant precipitate was collected
  4. customdried under vacuum
  5. customThis solid was purified by radial chromatography (2 mm silica)
  6. washeluting with a gradient of dichloromethane containing 5-7.5% methanol and 0.5-1.0% ammonium hydroxide
  7. customThe product was then crystallized from ethyl acetate

Sources & evidence

ORD record
ord-3d1472a252534bf687278fd38c1aea74
Source dataset
uspto-grants-1999_10
Patent number
US05962473

Reaction notes

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