Sodium Iodide → HCID 22321763, compound

Participants

Reaction Conditions

Reaction Steps

1-Boc-piperazine (6.8 g, 36 mmol), NaI (2.7 g, 18 mmol), K2CO3 (3.0 g, 21.6 mmol) and a mixture of 2-cyano-4-[2-(benzenesulfonyloxy)ethyl]pyridine and 2-cyano-4-(2-chloroethyl)pyridine (2:1, 4.5 g, 18 mmol) was dissolved in DMF (50mL) and heated to 80° C. overnight. The mixture was allowed to cool to room temperature and diluted with water and ethyl acetate. The layers were separated and the water layer extracted with ethyl acetate. The organic layers were combined, washed with water and brine, dried (Na2SO4), filtered and concentrated under vacuum to proved a dark oil (6.0 g). The crude product was purified by chromatography (SiO2, 1000:10:1-200:10:1 CH2Cl2:methanol:concentrated ammonium hydroxide) to provide 1-Boc-4-[2-(2-cyanopyridin-4-yl)ethyl]piperazine (4.0 g, 70%).

Provenance & Evidence