1-Chloroethyl chloroformate → HCID 53930236, compound

Participants

Reaction Steps

To a solution of 1.6 g of ethyl 3-(1-benzylpiperidin-4-yl)propenoate in 1,2-dichloroethane (30 ml) was added at 0° C. 0.74 ml of 1-chloroethyl chloroformate and the resulting mixture was stirred at the same temperature for 15 minutes and then heated under reflux for 1 hour. After distilling off the solvent under reduced pressure, 50 ml of methanol was added to the residue and the resulting mixture was heated under reflux for 1 hour. Then the mixture was made weakly alkaline with a dilute aqueous solution of sodium hydroxide and the solvent was distilled off under reduced pressure. To a solution of 1.0 g of ethyl 3-(piperidin-4-yl)propenoate thus obtained and 0.64 g of 8-(chloroethyl)-1OH-pyrazino[2,3-b][1,4]benzothiazine in N,N-dimethylformamide (30 ml) was added 1.1 g of anhydrous potassium carbonate and the resulting mixture was stirred by heating to 60° C. for 1 hour. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with methanol/dichloromethane) to thereby give 0.6 g of the title compound as yellow crystals.

Provenance & Evidence