Potassium Carbonate → HCID 11827083, compound

Participants

Reaction Steps

To a mixture of the above alcohol (1.3 g, 3.7 mmol), triethylamine (1.3 ml) and dry diethyl ether (75 ml) was added dropwise a solution of methanesulfonyl chloride (0.63 g, 5.5 mmol) in dry diethyl ether (25 ml). Stirring was continued for 1 h at room temperature. The reaction mixture was washed with water and dried over potassium carbonate. The solvent was evaporated in vacuo to give an oily residue which was dissolved in acetone (30 ml). To this solution was added potassium carbonate (1.0 g, 7.4 mmol) and ethyl (R)-3-piperidinecarboxylate (1.2 g, 7.4 mmol) and the suspension was heated at reflux temperature for 16 h. Another portion of ethyl (R)-3-piperidinecarboxylate (0.5 g) was added and the mixture was heated at reflux temperature for 24 h. This cooled reaction mixture was filtered and from the filtrate the solvent was evaporated in vacuo. This afforded an oil which was submitted to column chromatography on silica gel (100 g) using a mixture of ethyl acetate and n-heptane (1:1) as eluent. Collecting the proper fractions gave 1.5 g of (R)-N-(2-(2-(3,7-dichloro-10,11-dihydro-5H-dibenz[b,f]-azepin-5-yl)ethoxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil. TLC: rf=0.18 (SiO2 ; ethyl acetate/n-heptane=1:1 ).

Provenance & Evidence