1,8-Diaminonaphthalene → 4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride

Participants

Reaction Steps

Dissolve 1-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine (263.3 mg, 1.00 equiv; 0.662 mmoles) and 1,8-Naphthalenediamine, N,N,N′,N′-Tetramethyl-(0.05 equiv, 0.033 mmoles, 7.0 mg) in 1,2-Dichloro-ethane (5 mL) and cool in an ice bath. Add 1-chloroethyl chloroformate (1.2 equiv, 0.794 mmol; 0.086 mL). Stir the reaction 10 minutes in an ice bath then heat to reflux for 20 minutes and evaporate to dryness. Dissolve the residue in methanol (5 mL) and reflux for 45 minutes and evaporate to dryness to give 268 mg (0.779 mmol, 118%) 4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride.

Provenance & Evidence