HCID 59511218, compound → HCID 59511318, compound

HRID 1157328Notes

Reaction equation

HRID 1157328 reaction equation
[C:1]1([N:7]2[CH2:11][CH2:10][N:9]=[C:8]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1C=CC=CC=1.[O-2].[O-2].[O-2].[Ni+3].[Ni+3]>[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 59511218HCID 59511218, compound

Product 1

HCID 59511318HCID 59511318, compound

Reagents, catalysts & solvents 2

HCID 10313272Nickel oxide (Ni2O3)CatalystHCID 241BenzeneSolvent2×

Procedure

To a stirred solution of tert-butyl 4-(1-phenyl-4,5-dihydro-1H-imidazol-2-yl)piperidine-1-carboxylate (100 mg) in dry benzene (5 ml), nickel peroxide (350 mg) dissolved in dry benzene (20 ml) was added. The reaction mixture was refluxed for over-night and filtered through a celite pad using CHCl3 as eluent. The combined organic layer was removed under reduced pressure. The resulting oil was purified by column chromatography using ethyl acetate\hexane (3:7) to afford tert-butyl 4-(1-phenyl-1H-imidazol-2-yl)piperidine-1-carboxylate as pure product

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for over-night
  3. filtrationfiltered through a celite pad
  4. customThe combined organic layer was removed under reduced pressure
  5. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-8cbf5b3592854ef28aee69bef37b0778
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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