Acetic Acid → HCID 22319004, compound

HRID 229698Notes

Reaction equation

HRID 229698 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([CH2:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)(=O)C>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:28])[N:11]([CH2:21][CH:22]2[CH2:23][CH2:24][N:25]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:26][CH2:27]2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 22318995HCID 22318995, compound

Product 1

HCID 22319004HCID 22319004, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

80 mg of 3-(2-cyanophenyl)-1-(piperidin-4-yl)methyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 2 ml of chloroform. To the mixture were added 73 mg of benzaldehyde, 97 mg of triacetoxy sodium borohydride and 41 mg of acetic acid, followed by stirring at room temperature for 4 hours. The reaction solution was diluted with chloroform, and washed with a saturated aqueous solution of sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate. Then the mixture was evaporated, and the residue was purified by NH silica gel chromatography (hexane/ethyl acetate system), to give 80 mg of the title compound.

Workup

  1. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThen the mixture was evaporated
  4. customthe residue was purified by NH silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-6704d1ac5de24cc8baf18fba8ac0c6f9
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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