2-Piperidone → HCID 58247780, compound

HRID 714276Notes

Reaction equation

HRID 714276 reaction equation
[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[C:12](Cl)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=[O:24].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=[O:24])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 126652-PiperidoneHCID 15115857N-benzyl-2-chloropyridine-4-carboxamideHCID 23676156Sodium t-butoxide

Product 1

HCID 58247780HCID 58247780, compoundYield 21.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of N-benzyl-2-chloroisonicotinamide (0.30 g, 1.22 mmol), piperidin-2-one (0.12 g, 1.22 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.03 g, 0.05 mmol), palladium acetate (0.01 g, 0.05 mmol) and sodium tert-butoxide (0.12 g, 1.22 mmol) in toluene (10 mL) was heated at 130° C. for 36 hours under nitrogen atmosphere and concentrated in vacuo to dryness. The residue was dissolved in dichloromethane (50 mL) and washed with water (30 mL). The separated organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with 65-75% ethyl acetate in petroleum ether to give N-benzyl-2-(2-oxopiperidin-1-yl)isonicotinamide as a colorless solid (0.08 g, 21%): MS (ES+) m/z 310.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. washwashed with water (30 mL)
  4. dry with materialThe separated organic solution was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with 65-75% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-5650f70133d549a99796b96f912482c0
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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