HCID 58270830, compound → HCID 67108946, compound

HRID 222245Notes

Reaction equation

HRID 222245 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH2:9][NH:10][C:11]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)=O)=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:29][C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:15][CH2:14]3)=[N:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 58270830HCID 58270830, compound

Product 1

HCID 67108946HCID 67108946, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

To benzyl 4-{[2-(4-fluorophenyl)-2-oxoethyl]carbamoyl}piperidine-1-carboxylate (5.5 g) was added phosphorous oxychloride (20 mL), followed by stirring at 80° C. for 3 hours. After leaving to be cooled, the reaction liquid was concentrated under reduced pressure, and the residue was azeotroped with toluene three times. To the residue were added ethyl acetate and water, and the organic phase was separated. The organic phase was washed with a saturated aqueous sodium bicarbonate and saturated brine in this order, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 30/70) to obtain benzyl 4-[5-(4-fluorophenyl)-1,3-oxazol-2-yl]piperidine-1-carboxylate (1.84 g) as a colorless oily substance.

Workup

  1. customAfter leaving
  2. temperatureto be cooled
  3. customthe reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was azeotroped with toluene three times
  6. additionTo the residue were added ethyl acetate and water
  7. customthe organic phase was separated
  8. washThe organic phase was washed with a saturated aqueous sodium bicarbonate and saturated brine in this order
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 30/70)

Sources & evidence

ORD record
ord-8476ebb182d048a2addd1062affb350e
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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