Ceric ammonium nitrate → N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoyl]piperidine

HRID 1245215Notes

Reaction equation

HRID 1245215 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[CH:8]=[CH:9][C:10]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].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[CH:8]=[CH:9][C:10]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[C:11]([CH:20]=2)[C:12]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[O:13])[C:27](=[O:34])[C:28]=1[O:32][CH3:33]

Participants

6

Reactant 3

HCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 21919195N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoyl]piperidine

Product 1

HCID 21919203N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoyl]piperidineYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoyl]piperidine (33 mg, 0.0673 mmol) was dissolved in a mixed solvent of acetonitrile (6 ml) and water (2 ml), then CAN (92 mg, 0.1678 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 (methylene chloride:methanol=95:5) to give the title compound (20 mg, 0.0434 mmol, 64%).

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 (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-5f3af481cd664de091812eec38d77231
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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