HCID 59511173, compound → HCID 59511163, compound

HRID 1157821Notes

Reaction equation

HRID 1157821 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][N:16]=[C:15]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1C=CC=CC=1.[O-2].[O-2].[O-2].[Ni+3].[Ni+3]>[C:19]1([C:15]2[N:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)[CH:18]=[CH:17][N:16]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 59511173HCID 59511173, compound

Product 1

HCID 59511163HCID 59511163, compound

Reagents, catalysts & solvents 2

HCID 10313272Nickel oxide (Ni2O3)CatalystHCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl-4-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)piperidine-1-carboxylate (0.1 g) and nickel peroxide was dissolved in dry benzene (20 ml) and refluxed at 100° C. for over-night. Reaction mixture was allowed to come to room temperature, filtered through a celite pad and washed with CHCl3 (2×20 ml). The organic solvent removed under reduced pressure gave an oil, which was purified by column chromatography using ethyl acetate. Evaporation of solvent gave pure product, tert-butyl 4-(2-phenyl-1H-imidazol-1-yl)piperidine-1-carboxylate.

Workup

  1. customReaction mixture
  2. customto come to room temperature
  3. filtrationfiltered through a celite pad
  4. washwashed with CHCl3 (2×20 ml)
  5. customThe organic solvent removed under reduced pressure
  6. customgave an oil, which
  7. customwas purified by column chromatography
  8. customEvaporation of solvent

Sources & evidence

ORD record
ord-2c1f8e0711864e419591f41b2323d148
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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