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

HRID 1436866Notes

Reaction equation

HRID 1436866 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 stirred solution of 1-(4-fluorobenzyl)-3-(phenylsulfinyl)piperidin-2-one one (25 g, 74 mmol) in toluene (200 mL) was added anhydrous sodium carbonate (20 g, 190 mmol). The mixture was heated to reflux for 1.5 hours. The reaction mixture was cooled to ambient temperature and the solids were removed by filtration. The filtrate solvent was removed under vacuum and the residue was purified using silica gel column chromatography eluting with 3:1 EtOAc:hexanes. Appropriate fractions were combined and removal of the solvents under vacuum gave the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 2H), 7.01 (m, 2H), 6.56 (dt, J=9.9, 4.2 Hz, 1H), 6.00 (dt, J=9.7, 1.8 Hz, 1H), 4.59 (s, 2H), 3.32 (t, J=7.2 Hz, 2H), 2.33 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. customthe solids were removed by filtration
  4. customThe filtrate solvent was removed under vacuum
  5. customthe residue was purified
  6. washeluting with 3:1 EtOAc
  7. customremoval of the solvents under vacuum

Sources & evidence

ORD record
ord-d39c92291ee846b59b3c756bad62b4bc
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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