110-89-4

141-30-0

1722-11-8

GENERAL METHOD: Anhydrous ethanol (5 mL) and 3,6-dichloropyridazine (3.36 mmol) were added to a 50 mL round-bottomed flask, followed by triethylamine (5.03 mmol) and hexahydropyridine (5.03 mmol). The reaction mixture was stirred under ethanol reflux conditions for 3,6-dichloropyridazine and 3,6-dichloropyrazine and at room temperature for 3,6-dichloropyrimidine. The reaction process was monitored by gas chromatography (GC). When the starting material 3,6-dichloropyridazine was completely consumed, the reaction mixture was poured into saturated ammonium chloride solution (20 mL) and extracted with dichloromethane (3 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was ground with petroleum ether and filtered through a Büchner funnel to give pure 1-(6-chloropyridazin-3-yl)piperidine.