5308-25-8

149806-06-4

1231930-25-8

To 100 mL of anhydrous dichloromethane (DCM) were added N-ethylpiperazine (10 g, 54 mmol) and 2-bromo-5-formylpyridine (6.20 g, 54.00 mmol) followed by batchwise addition of sodium triacetoxyborohydride (NaHB(OAc)3, 17.20 g, 81.00 mmol). The reaction mixture was stirred at room temperature for 5 hours. Upon completion of the reaction, the mixture was diluted with DCM (100 mL) and the pH was adjusted to 8-10 by adding saturated sodium carbonate (Na2CO3) solution. the mixture was partitioned between water and dichloromethane. The aqueous phase was extracted twice with dichloromethane. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated in vacuum. The crude product was purified by silica gel column chromatography (eluent: DCM/MeOH = 50:1) to afford the target compound 1-((6-bromopyridin-3-yl)methyl)-4-ethylpiperazine (8a, 14.00 g, 92.00% yield) as a yellow solid. Mass spectrum (ESI): calculated value C12H18BrN3 [M+H]+ 284, measured value 284.