Ceric ammonium nitrate → HCID 21919205, compound

HRID 1245228Notes

Reaction equation

HRID 1245228 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:22]=[N:23][CH:24]=[CH:25][CH:26]=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]=[N:23][CH: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 21919193HCID 21919193, compound

Product 1

HCID 21919205HCID 21919205, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-[3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoyl]piperidine (80 mg, 0.1632 mmol) was dissolved in a mixed solvent of acetonitrile (9 ml) and water (3 ml), then CAN (128 mg, 0.2335 mmol) was added thereto at room temperature and the mixture was stirred for 1 hour. The reaction solution 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=1:3) to give the title compound (51 mg, 0.1108 mmol, 68%). This compound was converted to a methanesulfonate by the method according to Example 58.

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=1:3)

Sources & evidence

ORD record
ord-48f93f681c6d4f6ca155a329f4c721fd
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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