Ethyl Acetate → HCID 178451791, compound

Participants

Reaction Steps

Suspend 4-Diaminomethyl-piperidine-1-carboxylic acid tert-butyl ester acetic acid salt (685 mg; 1.00 equiv; 2.38 mmoles) in dimethylformamide (10 mL; 129.33 mmoles) and add powdered potassium carbonate (1400 mg; 10.13 mmoles). Stir 10 minutes at room temperature then add 2-Bromo-1-(3-chloro-phenyl)-ethanone (1400 mg; 6.00 mmoles) dissolved in 4 mL DMF dropwise to the amidine at room temperature. After 3 h, dilute the reaction with ethyl acetate and wash with 50% aq. sodium bicarbonate. Dry the organic layer over sodium sulfate, filter and concentrate to a crude oil. Purify using ISCO chromatography over a biotage 40M column, eluting with a gradient of DCM to 6% MeOH/DCM. Concentrate the appropriate fractions to give a 20% yield of 4-[4-(3-Chloro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester. MS (ES): m/z=262.0 [M+H].

Provenance & Evidence