Sodium hydride → Methyl 3-(2-oxopiperidin-1-yl)benzoate

HRID 2335Notes

Reaction equation

HRID 2335 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])=[O:7].[H-].[Na+]>CN(C=O)C>[O:7]=[C:6]1[CH2:5][CH2:4][CH2:3][CH2:2][N:8]1[C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 10686692Methyl 3-(5-bromopentanoylamino)benzoate

Product 1

HCID 10681135Methyl 3-(2-oxopiperidin-1-yl)benzoateYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The bromide of Example 36 (1.50 g, 4.88 mmol) was taken up in dry DMF (40 ml) and treated with NaH (160 mg, 80% disp. in oil) at 0° C. The mixture was stirred at r.t. under nitrogen for 10 min, then KI (80 mg) added and the mixture heated at 70° C. for 4 h. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1 PS, phase separator) and evaporated. The residue was chromatographed (eluant 2% MeOH in EtOAc) to provide a colourless oil (640 mg, 56%).

Workup

  1. additionKI (80 mg) added
  2. temperaturethe mixture heated at 70° C. for 4 h
  3. customThe mixture was evaporated
  4. custompartitioned between EtOAc and 1M HCl
  5. washThe organic portion was washed with 5% KHCO3 and brine
  6. filtrationfiltered (Whatman® 1 PS, phase separator)
  7. customevaporated
  8. customThe residue was chromatographed (eluant 2% MeOH in EtOAc)

Sources & evidence

ORD record
ord-39e2a12366cc4afaa1054c2e96602afd
Source dataset
uspto-grants-1998_03
Patent number
US05728829

Reaction notes

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