Piperidine → 5-Nitro-2-piperidinopyridine

Participants

Reaction Steps

2-Chloro-5-nitropyridine (10 g, 63.3 mmol) was dissolved in 150 mL of THF. 20 mL of piperidine was then added and the resulting mixture was stirred for 18 hours at room temperature. The reaction mixture with copious precipitate was then diluted with 200 mL of water and 100 mL of diethyl ether. The layers were thoroughly mixed and separated. The organic layer was dried over sodium sulfate and concentrated in vacuo. The bright yellow solid was redissolved in 35 mL of dichloromethane and, with vigorous stirring, hexanes were added until the product began to precipitate. The bright yellow solid was collected by filtration and dried to afford 12.5 g of 5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl.

Provenance & Evidence