Ethanol → Methyl 2-fluoro-5-(4-oxopiperidin-1-yl)benzoate

HRID 406390Notes

Reaction equation

HRID 406390 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].C([N+]1(C)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1)C1C=CC=CC=1.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]([F:34])=[C:28]([CH:33]=1)[C:29]([O:31][CH3:32])=[O:30].C(O)C>O>[F:34][C:27]1[CH:26]=[CH:25][C:24]([N:23]2[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 110780641-Benzyl-1-methyl-4-oxopiperidinium iodideHCID 15621043Methyl 5-amino-2-fluorobenzoate

Product 1

HCID 66619019Methyl 2-fluoro-5-(4-oxopiperidin-1-yl)benzoateYield 67.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Potassium carbonate (149 mg) and 1-benzyl-1-methyl-4-oxopiperidinium iodide (2.87 g) were sequentially added to a solution of methyl 5-amino-2-fluorobenzoate (1.22 g) obtained in Preparation Example 6-1 in a mixed solvent of ethanol 10 ml) and water (5 ml). The reaction mixture was refluxed for 2.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.22 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a05c0bafdf504e81835124e1c1ca8cfc
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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