Methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoate → Methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxopiperidin-3-yl}benzoate

HRID 910618Notes

Reaction equation

HRID 910618 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:6]1=[O:21].[H][H]>C(O)(=O)C.[Pt]=O>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)[C:6]1=[O:21]

Participants

5

Reactant 2

HCID 57584036Methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 57584008Methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxopiperidin-3-yl}benzoateYield 88.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoate (490 mg) was dissolved in acetic acid (20 mL), and platinum oxide (74 mg) was added, followed by stirring in a hydrogen atmosphere (1 atm.) at room temperature for 15 hours. The vapor in the reactor was purged with argon, then the reaction mixture was filtered through Celite, followed by washing with methanol. The filtrate was concentrated under reduced pressure, followed by two times azeotropy with toluene. An aqueous saturated sodium hydrogencarbonate solution was added to the residue, followed by two times extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2) to obtain methyl 4-{1-[2-(dimethylamino)ethyl]-2-oxopiperidin-3-yl}benzoate (439 mg) as a colorless oil.

Workup

  1. customThe vapor in the reactor was purged with argon
  2. filtrationthe reaction mixture was filtered through Celite
  3. washby washing with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionAn aqueous saturated sodium hydrogencarbonate solution was added to the residue
  6. extractionfollowed by two times extraction with chloroform
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customthe resulting residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:2)

Sources & evidence

ORD record
ord-3f5e8a404fdc4ed989e5613f4a6c9e32
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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