Potassium Iodide → HCID 10957911, compound

Participants

Reaction Conditions

Reaction Steps

6-Aminohexanol (15 mmol), 4-chloroquinoline (15 mmol), 5 ml of triethylamine and catalytic amounts of potassium iodide were refluxed in ethanol for 12 hours. The solvent was evaporated and the residue was purified by flash chromatography on silica gel (eluent: methylene chloride/methanol (98/2), ammonia atmosphere). The solvent was removed under reduced pressure. At 0° C. the product (5 mmol) was added to thionyl chloride (10 mmol). The temperature was raised to 70° C. for three hours. Excess thionyl chloride was evaporated. The residue was recrystallized from diethyl ether/ethanol. The product (5 mmol), piperidine (10 mmol), potassium carbonate (15 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 12 hours. The solvent was evaporated and the residue purified by flash chromatography (eluent: ethyl acetate/methanol/triethylamine (95/5/2)). The solvent was removed under reduced pressure. The residue was crystallized with oxalic acid from diethyl ether/ethanol.

Provenance & Evidence