Sodium Carbonate → 1-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

HRID 1817292Notes

Reaction equation

HRID 1817292 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH:9](S(C3C=CC=CC=3)=O)[C:8]2=[O:21])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2=[O:21])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 690624651-(4-Fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one

Product 1

HCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one (0.37 g, 1.11 mmol) in toluene (15 mL) was added solid Na2CO3 (2 g, 18.8 mmol). The reaction mixture was refluxed for about 6 hours. The resultant solution was filtered and concentrated under vacuum and the residue chromatographed on silica eluting with a gradient of 040% EtOAc/Hexanes to give the product as colorless glass.

Workup

  1. temperatureThe reaction mixture was refluxed for about 6 hours
  2. filtrationThe resultant solution was filtered
  3. concentrationconcentrated under vacuum
  4. customthe residue chromatographed on silica eluting with a gradient of 040% EtOAc/Hexanes

Sources & evidence

ORD record
ord-b00db7f51e88446f9549554366979b1f
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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