Potassium Hydroxide → HCID 18797384, compound

HRID 1456961Notes

Reaction equation

HRID 1456961 reaction equation
[OH-].[K+].[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)#[N:4].[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:24]1[CH2:25][CH2:26][N:21]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:22][CH:23]=1)#[N:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 27513Indole-5-carbonitrile

Product 1

HCID 18797384HCID 18797384, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.02 gm (89.0 mMol) potassium hydroxide in 50 mL methanol were added 5.00 gm (35.17 mmol) 5-cyano-1H-indole and 7.8 mL (42.08 mmol) 1-benzyl-4-piperidone. The reaction mixture was stirred for 16 hours at reflux and then was allowed to cool. The reaction mixture was then concentrated under reduced pressure. The resultant residue was subjected to flash chromatography, eluting with dichloromethane containing 5% methanol. Fractions shown to contain product were combined and concentrated under reduced pressure to give 11.0 gm of the title compound of sufficient purity to be used in subsequent reactions.

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. washeluting with dichloromethane containing 5% methanol
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92fcd9c486e145ce90dd75f929d46ffb
Source dataset
uspto-grants-1998_12
Patent number
US05846982

Reaction notes

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