Quipazine → Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate

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Reaction Steps

A mixture of 66.5 g of 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylic acid ethyl ester as synthesized in above Step 7-1-C, 46.9 g of 2-piperazin-1-ylquinoline as synthesized in above Step 7-1-A, 22.3 g of triethylamine and 350 ml of toluene was heated under reflux for an overnight. The solvent was concentrated under reduced pressure, and ethyl acetate was added to the residue, followed by washing with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2) to provide 79.8 g (86%) of 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylic acid ethyl ester.

Provenance & Evidence