3,4-Diaminoquinoline → HCID 10661633, compound

In 330 ml of pyridine was dissolved 5.52 g (34.7 mmol) of 3,4-diaminoquinoline. To the solution was slowly added 7.70 g (36.5 mmol) of 5-chlorocarbonyl-1-azabicyclo[3.3.0]octane hydrochloride while stirring at -15° to 20° C., followed by stirring at 15 to 20° C. for 16 hours. The reaction mixture was concentrated under reduced pressure, and 100 ml of a saturated sodium hydrogen-carbonate aqueous solution was added to the residue. The mixture was extracted with 800 ml of chloroform. The extract was washed with 40.0 ml of a sodium chloride aqueous solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by alumina column chromatography to obtain 4.30 g (yield: 41.8%) of the titled compound as an oil. The resulting oil was crystallized from ethanol-diethyl ether to obtain 3.05 g of the titled compound as a pale yellow prism.

1. stirringby stirring at 15 to 20° C. for 16 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure, and 100 ml of a saturated sodium hydrogen-carbonate aqueous solution
3. additionwas added to the residue
4. extractionThe mixture was extracted with 800 ml of chloroform
5. washThe extract was washed with 40.0 ml of a sodium chloride aqueous solution
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by alumina column chromatography

ORD record

ord-f25cdfa4d7734f3b96dd4b6e5ec30e3d

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05434165