Diethylcarbamoyl chloride → HCID 13077557, compound

Participants

Reaction Steps

To a mixture of 2.4 g (0.00673 mole) of 6-methoxy-4-methyl-N-[6-(1-piperazinyl)hexyl]-8-quinolinamine and 1.7 g (0.016 mole) of sodium carbonate in 50 ml of acetone was added a solution of 1.8 g (0.007 mole) of diethylcarbamoylchloride in 20 ml of acetone. The mixture was stirred under gentle reflux for 2 hr, allowed to cool, filtered and concentrated to dryness in vacuo. A solution of the residue in dichloromethane was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Chromatography of the residue over 70 g of silica with 10% methanol in ethyl acetate afforded 2 g of product, Rf=0.3. The material was triturated with 2-propanol containing excess hydrogen chloride. The resulting yellow precipitate was collected, washed with 2-propanol and then ether, dried in vacuo at 52° overnight and air-equilibrated to afford 1.8 g (50%) of the title compound, mp 226°-228° (dec).

Provenance & Evidence