Acetonitrile → 1-(5-Carboxy-pentyl)-4-methyl-quinolinium iodide

To a 250 mL flask were added lepidine (7.5 g, 52.4 mmol), acetonitrile (40 mL) and 6-iodohexanoic acid (14.0 g, 57.9 mmol). The mixture was heated at reflux under argon for 40 h and then was cooled to rt. The mixture was poured into stirred ether (700 mL) and the stirring was continued until the supernatant liquid was clear. The supernatant was decanted and the residue was dissolved in DCM (60 mL). The solution was poured slowly into stirred ether (700 mL). The initially formed oil solidified after stirring for approx. 3 h. The solid was crushed to a powder and stirring was continued for 1 h. The solid was filtered off, washed with ether (2×60 mL), and dried under vacuum to afford 14 as a tan colored solid (17.6 g, 87%).

1. temperatureThe mixture was heated
2. temperatureat reflux under argon for 40 h
3. additionThe mixture was poured
4. customThe supernatant was decanted
5. dissolutionthe residue was dissolved in DCM (60 mL)
6. additionThe solution was poured slowly
7. stirringafter stirring for approx. 3 h
8. customThe solid was crushed to a powder
9. stirringstirring
10. filtrationThe solid was filtered off
11. washwashed with ether (2×60 mL)
12. customdried under vacuum

ORD record

ord-fea76d1dfc46449785e809107deed035

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07868157B2