Pyridine → N-ethyl-4-farnesylacetoxy-piperidine

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In a 200-ml three-necked flask equipped with dropping funnel, thermometer and reflux condenser, there were placed 4.80 g of N-ethyl-4-hydroxypiperidine, 3.23 g of pyridine and 50 ml of benzene, and 11.60 g of farnesylacetyl chloride was added dropwise under reflux. After completion of the dropping, the mixture was refluxed for a subsequent 2 hour period and then cooled. Addition of 30 ml of 20% aqueous solution of sodium hydroxide, stirring, phase separation and silica gel column chromatography of the upper layer yielded 2.4 g of N-ethyl-4-farnesylacetoxy-piperidine as a pale-yellow liquid. The product was identified by proton NMR and mass spectrometry. The proton NMR data are shown in the following.

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