1-Methyl-4-piperidone → HCID 70105927, compound

HRID 843878Notes

Reaction equation

HRID 843878 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([NH2:17])[CH:12]=[CH:11]3)=[O:7])=[CH:4][CH:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1>[OH-].[K+]>[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([NH2:17])[CH:12]=[C:11]3[C:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH:23]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 740491-Methyl-4-piperidoneHCID 70120627HCID 70120627, compound

Product 1

HCID 70105927HCID 70105927, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of 2.54 gm (10 mMol) 5-(4-fluorobenzoyl)-amino-1H-indole and 1.7 gm (15.0 mMol) 1-methyl-4-piperidone in 20 mL 10% methanolic potassium hydroxide was heated to reflux for 3.5 hours and then allowed to stir without heating. After 18 hours the resultant suspension was filtered, the solid washed with methanol and then dried under reduced pressure to give 2.30 gm (65.8%) 5-(4-fluorobenzoyl)-amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole as a tan powder.

Workup

  1. temperatureto reflux for 3.5 hours
  2. temperaturewithout heating
  3. filtrationAfter 18 hours the resultant suspension was filtered
  4. washthe solid washed with methanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-b409b64bc96b48ad922998c3c409591a
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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