Ceric ammonium nitrate → HCID 22054189, compound

HRID 1830273Notes

Reaction equation

HRID 1830273 reaction equation
C[O:2][C:3]1[C:4]([CH3:38])=[C:5]([C:29]([O:36]C)=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[C:9]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:8]=1.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(#N)C.O>[CH3:33][O:32][C:31]1[C:3](=[O:2])[C:4]([CH3:38])=[C:5]([CH2:6][C:7]2[CH:20]=[CH:19][C:10]([C:11]([N:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)=[O:12])=[C:9]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:8]=2)[C:29](=[O:36])[C:30]=1[O:34][CH3:35]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 22054167HCID 22054167, compound

Product 1

HCID 22054189HCID 22054189, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-[4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoyl]piperidine (129 mg, 0.2485 mmol) was dissolved in a mixed solution of acetonitrile (15 ml) and water (5 ml) and after adding thereto CAN (341 mg, 0.6222 mmol) at room temperature, the solution was stirred at room temperature for 1 hour. The reaction solution was diluted with water and then extracted with ether. The extract was washed with water and then dried, and the solvent was removed by distillation. The residue was purified by flash column chromatography (hexand:ethyl acetate=2:1) to obtain the titled compound (85 mg, 0.1738 mmol, 70%).

Workup

  1. additionafter adding
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was removed by distillation
  6. customThe residue was purified by flash column chromatography (hexand:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-095503ebaf4d437788644946424537a0
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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