Hydrochloric Acid → Oleic acid-2-{[3-(4-amino-piperidin-1-yl)-propyl]-(2-oleoyloxy-ethyl)-amino}-ethyl ester

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Reaction Steps

A suspension of 4.5 g (4 mmol) of the 2-{[3-(4-amino-piperidin-1-yl)-propyl]-(2-hydroxy-ethyl)-amino}-ethanol-hydrochloride described in example 10 in 100 ml dichloromethane is admixed with 3.5 g N-ethyl-diisopropylamine and 0.87 g (4 mmol) pyrocarbonic acid di-t-butyl ester, it is refluxed for 18 h, a solution of 2.4 g (8 mmol) oleoyl chloride in 40 ml dichloromethane is added dropwise, it is refluxed for 18 h, admixed with 15 ml etheric hydrogen chloride solution and stirred for 6 h at room temperature. It is concentrated by evaporation, adjusted to pH 9 with N sodium hydroxide solution, extracted with dichloromethane and methanol, dried and concentrated by evaporation. After chromatography on silica gel (eluting agent ethyl acetate/methanol 1:1) 1.1 g (36% of theory) of the title compound is isolated as an oil.

Provenance & Evidence