Potassium Carbonate → HCID 11069527, compound

Participants

Reaction Steps

To a solution of 2-(((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)amino)oxy)ethylbromide (1.4 g, 4.2 mmol) in methyl isobutylketone (40 ml) was added potassium carbonate (4.7 g, 34 mmol) and ethyl (R)-3-piperidinecarboxylate tartrate (2.6 g, 8.5 mmol) and the suspension was heated at reflux temperature for 3 days. The cooled reaction mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The oily residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml). A 34% aqueous tartaric acid solution was added until pH 4. The phases were separated and the aqueous phase was extracted with ethyl acetate (25 ml). The combined organic phases were extracted with a 34% aqueous tartaric 1/2acid solution (2×5 ml) and the organic extracts were discarded. The acidic aqueous phases were combined, diluted three times with water and ethyl acetate (40 ml) was added. A 4 N sodium hydroxide solution was added until pH 7 and the phases were separated. The organic phase was washed with brine and dried over sodium sulphate. The solvent was evaporated in vacuo to give 1 g of (R)-N-(2-(((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil. TLC: rf=0.39 (SiO2 ; dichloromethane/methanol/acetic acid=20:2:1).

Provenance & Evidence