Dimethyl Sulfoxide → 1-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine

Participants

Reaction Steps

Add dimethyl sulfoxide (0.3 M, 2.7 mL) to powdered potassium hydroxide (1.5 equiv, 1.217 mmoles; 68 mg). Add 1-Benzyl-4-[5-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine (300 mg, 1.00 equiv; 0.811 mmoles), dropwise add iodoethane (1.1 equiv, 0.892 mmoles; 71 μL) over 8 min. Stir the reaction for 60 minutes, then dilute with water (120 mL) plus saturated sodium chloride (25 mL) and extract four times with DCM. Wash the organic extracts with water, then saturated aqueous sodium chloride, and dry with MgSO4. Filter and purify on silica gel with 10% methanol/acetonitrile to give 262 mg (0.659 mmol, 81%) of 1-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine.

Provenance & Evidence