Benzene, (2-bromoethoxy)- → ethyl N-(2-phenoxyethyl)piperidine-3-carboxylate

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Reaction Steps

A mixture of ethyl 3-piperidinecarboxylate (20.58 g), 2-bromoethyl phenyl ether (26.31 g), sodium bicarbonate (10.99 g) and IMS (100 ml) was boiled under reflux for 16 hours. The mixture was evaporated to dryness then diluted with water (100 ml) and 2M sodium hydroxide solution (20 ml). This mixture was extracted with dichloromethane and the combined dichloromethane extracts were extracted with 2M hydrochloric acid. The acidic extracts were washed with dichloromethane and then basified with 2M sodium hydroxide solution. This mixture was extracted with dichloromethane to give ethyl N-(2-phenoxyethyl)piperidine-3-carboxylate as an oil. A sample of the oil was dissolved in ether and ethereal oxalic acid was added. The precipitate was filtered off and recrystallised from aqueous propan-2-ol to give ethyl N-(2-phenoxyethyl)piperidine-3-carboxylate oxalate hemihydrate, m.p. 131°-132° C.

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