Acetic Acid → HCID 85618866, compound

Participants

Reaction Steps

Hydrogen bromide in acetic acid (5.0 mL of a 30% solution) was added to 3-(6-chloropyrazin-2-yl)-1-azabicyclo[2.2.2]octane (613 mg, 2.74 mmol; EPA 327155) and the solution was stirred at room temperature for 3.5 days. The mixture was poured into 0.5M potassium carbonate (75 mL) then further basified with solid potassium carbonate and extracted with dichloromethane (five times). The solvent was evaporated and the residue redissolved in hydrogen bromide/acetic acid (5.0 mL) and left stirring for 14 hours. The mixture was worked up as described above and crude product purified by column chromatography on silica using 10% methanol in dichloromethane containing 1% ammonia to afford the title compound free base (289 mg, 39%) as a colourless oil. The sesquioxalate salt had mp 173°-177° C. (dec) (methanol). MS, m/z 267 for M+ of free base. (Found: C, 41.70; H, 4.29; N, 10.40; Br, 20.32. C11H14BrN3.1.5C2H2O4 requires C, 41.70; H, 4.25; N, 10.42; Br, 19.82%).

Provenance & Evidence