Water → 3-[4-(2-Cyanophenyl)piperidin-1-yl]-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

HRID 497847Notes

Reaction equation

HRID 497847 reaction equation
Br[C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.O.[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1N1CCNCC1)#[N:23]>>[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:7]1[CH2:6][CH2:5][N:4]([C:2]2[C:3](=[O:20])[N:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:7]=2)[CH2:3][CH2:2]1)#[N:23]

Participants

4

Reactant 3

HCID 962WaterHCID 2735875N-(2-Cyanophenyl)piperazineHCID 223190653-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one

Product 1

HCID 223191873-[4-(2-Cyanophenyl)piperidin-1-yl]-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-oneYield 41.7%

Conditions

Temperature
130 °C

Procedure

29 mg of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 200 mg of 1-(2-cyanophenyl)piperazine, followed by heating at 130° C. for 72 hours. After the reaction solution was cooled to room temperature, water was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 8 mg of the title compound.

Workup

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. extractionby extracting with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-42fa339703ec48649dcadb401a833740
Source dataset
uspto-grants-2005_09
Patent number
US06949571B2

Reaction notes

Loading…