2-Phenylimidazole → 2-Cyclohexyl-1H-imidazole

HRID 277715Notes

Reaction equation

HRID 277715 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl.[Rh]>[CH:1]1([C:7]2[NH:11][CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 695912-Phenylimidazole

Product 1

HCID 111594052-Cyclohexyl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 6.8 g of 2-phenylimidazole in 200 mL 3N hydrochloric acid was added 5% Rhodium on Carbon, Degussa type G10 NB/W. The mixture was hydrogenated at 100 psi for 24 hours then filtered through celite. The solution was neutralized with 25% sodium hydroxide and extracted with 2×100 mL ethyl acetate. The combined extract was washed with 200 mL of brine and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 2-cyclohexylimidazole as a fluffy, white solid which was used in the next step without further purification or characterization.

Workup

  1. filtrationthen filtered through celite
  2. extractionextracted with 2×100 mL ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with 200 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f7e0a6c0600e4c4cabedd7430e3218fd
Source dataset
uspto-grants-2002_03
Patent number
US06358955B1

Reaction notes

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