Phenol → HCID 20131119, compound

Participants

Reaction Steps

4-Amino-2-[4-(2-chloropyrimidin-4-yl)piperazin-1-yl]-6,7-dimethoxyquinoline hemihydrate (0.32 g), phenol (0.15 g), anhydrous potassium carbonate (0.22 g) and potassium iodide (catalytic trace) in 4-methyl-2-pentanone (125 ml) were stirred under reflux for 18 hours. Further portions of phenol, anhydrous potassium carbonate and potassium iodide were then added thrice at 8 hour intervals, followed by a final 18 hours refluxing. After cooling, methylene chloride (50 ml) and methanol (20 ml) were added and the reaction mixture filtered. The filtrate was evaporated in vacuo and the residue dissolved in methylene chloride, washed with water, dried (MgSO4) and evaporated in vacuo. Chromatography on silica (Merck 9385, 40 g) eluting with methylene chloride/methanol (100:0→88:12) followed by treatment of the product with ethereal hydrogen chloride and recrystallisation from isopropanol gave 4-amino-6,7-dimethoxy-2-[4-(2-phenoxypyrimidin-4-yl)piperazin-1-yl]quinoline dihydrochloride (0.26 g), m.p. 199°-201° (d).

Provenance & Evidence