Potassium Carbonate → HCID 10895908, compound

Participants

Reaction Steps

To a solution of 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propanol (3.5 g, 14 mmol) in benzene (50 ml), triethylamine (4 ml) and methanesulfonyl chloride (2.0 g, 17.4 mmol) were added and the reaction mixture was stirred at room temperature for 6 h. Water was added and the phases were separated. The organic phase was dried (MgSO4) and solvent was evaporated in vacuo to give a residue which was dissolved in 2-butanone (50 ml). Ethyl 4-phenyl-4-piperidine-carboxylate hydrobromide (4.4 g, 14 mmol) and potassium carbonate (4.4 g, 32 mmol) were added and the mixture was heated at reflux temperature for 24 h. The mixture was filtered and the solvent evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (50 g) using ethyl acetate as eluent to give 5.3 g of 1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)-4-phenyl-4-piperidinecarboxylic acid ethyl ester as an oil.

Provenance & Evidence