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

HRID 1737829Notes

Reaction equation

HRID 1737829 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-fc5711e7ba8644ccbf0bedd7103df8fb
Source dataset
uspto-grants-1999_10
Patent number
US05962474

Reaction notes

Loading…