Ethyl 4-piperidinecarboxylate → Ethyl 1-(2-cyano-4-nitrophenyl)piperidine-4-carboxylate

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Reaction Steps

2-Chloro-5-nitrobenzonitrile (10 g), ethyl isonipecotate (60 g) and silver nitrate (11.1 g) were stirred at 120° C. for 3 h. The reaction mixture was cooled to room temperature and the solid was filtered off. To the filtrate was added dilute hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous diisopropyl ether to give ethyl 1-(4-nitro-2-cyanophenyl)piperidin-4-ylcarboxylate (17.1 g).

Provenance & Evidence