Ammonium cerium (IV) nitrate → HCID 66608280, compound

HRID 1398236Notes

Reaction equation

HRID 1398236 reaction equation
COC1C=CC(C[N:8]2[CH2:13][CH2:12][CH2:11][C:10]([CH3:24])([O:14][C:15]3[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=3)[C:9]2=[O:25])=CC=1.[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(#N)C.O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:24][C:10]1([O:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=2)[CH2:11][CH2:12][CH2:13][NH:8][C:9]1=[O:25]

Participants

7

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrate2×HCID 666083191-(4-Methoxybenzyl)-3-methyl-3-(3,4,5-trifluorophenoxy)piperidin-2-one

Product 1

HCID 66608280HCID 66608280, compoundYield 57.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 1-(4-methoxybenzyl)-3-methyl-3-(3,4,5-trifluorophenoxy)piperidin-2-one (76.2 mg) in acetonitrile (1 mL) was added a mixture of cerium(IV) ammonium nitrate (275 mg) in water (1 mL) at room temperature, and the mixture was stirred overnight. Cerium(IV) ammonium nitrate (110 mg) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and the insoluble material was removed by filtration. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate) and silica gel column chromatography (ethyl acetate/hexane) to give the title compound (30.1 mg).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. customthe insoluble material was removed by filtration
  4. customThe organic layer was separated
  5. washwashed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate) and silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fec9040cfd7a4508bddfc27a17007392
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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