2-Chloropyridine → N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]pyridin-2-amine

Participants

Reaction Steps

23.5 g of 1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine [Hexachemie-Reuil Malmaison-France] and 4.85 mL of 2-chloropyridine were stirred at 160° C. in a closed reaction vessel for 10.5 hours. The reaction mixture was cooled to room temperature, dissolved in 320 mL of chloroform and washed with 1N sodium hydroxide (3×320 mL), followed by water (2×400 mL). The organic layer was dried (sodium sulfate) and evaporated to dryness under reduced pressure. The crude product was purified by column flash chromatography eluting with an ethyl acetate-3N NH3 in methanol 100:2 mixture affording, after evaporation of the collected fractions, 5 g of the title compound as an oil. A sample was crystallized from ethyl acetate to give a solid melting at 89-94° C.

Provenance & Evidence