Potassium Hydroxide → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carboxamide

HRID 641876Notes

Reaction equation

HRID 641876 reaction equation
[OH-:1].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH3:14][N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1>CO>[CH3:14][N:15]1[CH2:16][CH:17]=[C:18]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]([NH2:13])=[O:1])[CH:7]=3)[NH:3][CH:4]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27513Indole-5-carbonitrileHCID 740491-Methyl-4-piperidone

Product 1

HCID 149732133-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carboxamideYield 11.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of KOH (1.0 g, 17.68 mmol) in methanol (20 mL) was added to 1H-indole-5-carbonitrile (1.0 g, 6.96 mmol). 1-methylpiperidin-4-one (1.0 g, 8.75 mmol) was then added dropwise with stirring, while cooling to 0-5° C. and the resulting solution was stirred for 1 hour at 50° C. The reaction mixture was then cooled to room temperature, concentrated, and the residue was purified by column chromatography using ethanol solvent system to give 200 mg of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carboxamide as a white solid.

Workup

  1. stirringthe resulting solution was stirred for 1 hour at 50° C
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b91424bde1364b5d9aed030b42809dce
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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