Sodium Iodide → HCID 22321629, compound

Participants

Reaction Conditions

Reaction Steps

3-Fluoro-4-(2-methanesulfonyloxyethyl)pyridine (5.2 g, 23.7 mmol) was dissolved in DMF (65 mL). 1-Boc-piperazine (8.85 g, 47.4 mmol), K2CO3 (3.3 g, 23.7 mmol), NaI (3.6 g, 23.7 mmol) and Cs2CO3 (7.7 g, 23.7 mmol) were added, and the mixture heated to 55° C. for 18 h. The mixture was cooled 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 brine, dried (Na2SO4), filtered, and concentrated under vacuum to provide a solution of product and DMF. The residue was dissolved in diethyl ether and water. The layers were separated, and the water layer extracted with diethyl ether. The organic layers were combined, washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum. The crude product was purified by chromatography (SiO2, 15:1-6:1 CH2Cl2:CMA) to give 1-Boc-4-[2-(3-fluoropyridin-4-yl)ethyl]piperazine (6.2 g, 84%).

Provenance & Evidence