Ceric ammonium nitrate → N-[3-(5.6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridyl)benzoyl]piperidine

HRID 1245230Notes

Reaction equation

HRID 1245230 reaction equation
C[O:2][C:3]1[C:4]([CH3:36])=[C:5]([C:27]([O:34]C)=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH2:6][C:7]1[C:8]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:9]([CH:18]=[CH:19][CH:20]=1)[C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(=O)([O-])O.[Na+]>C(#N)C.O>[CH3:31][O:30][C:29]1[C:3](=[O:2])[C:4]([CH3:36])=[C:5]([CH2:6][C:7]2[C:8]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)=[C:9]([CH:18]=[CH:19][CH:20]=2)[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[C:27](=[O:34])[C:28]=1[O:32][CH3:33]

Participants

6

Reactant 3

HCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 21919137N-[3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]piperidine

Product 1

HCID 21919165N-[3-(5.6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(4-pyridyl)benzoyl]piperidineYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-[3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]piperidine (74 mg, 0.1510 mmol) was dissolved in a mixed solvent of acetonitrile (9 ml) and water (3 ml), then CAN (206 mg, 0.3759 mmol) was added thereto at room temperature and the mixture was stirred for 1 hour. The reaction solution was poured into water, neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by preparative thin layer silica gel (hexane:ethyl acetate=1:5) to give the title compound (32 mg, 0.0695 mmol, 46%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative thin layer silica gel (hexane:ethyl acetate=1:5)

Sources & evidence

ORD record
ord-3a977edc3b374ee294f8d238aec4b9ad
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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