Pyridine → Quipazine

A mixture of 2-chloroquinoline (10.0 g, 60.5 mmol), piperazine (26.1 g, 303 mmol) and pyridine (15 ml) was heated reflux temperature for 4 h. The hot reaction mixture was poured into a conical flask and diluted with tetrahydrofuran (150 ml). The precipitated solid was filtered off and washed with diethyl ether (3×50 ml) and the combined organic phases were evaporated in vacuo. The residue was suspended in a mixture of diethyl ether (200 ml) and 96% ethanol (80 ml) and undissolved solid was filtered off and washed with diethyl ether. The organic phase was evaporated in vacuo affording a solid which was crushed under water (200 ml) filtered off and washed with water (3×50 ml), diethyl ether (3×40 ml), dried in vacuo at 50° C. affording 11.8 g (92%) of 2-(1-piperazinyl)quinoline as a solid.

1. temperaturewas heated
2. temperaturereflux temperature for 4 h
3. additionThe hot reaction mixture was poured into a conical flask
4. filtrationThe precipitated solid was filtered off
5. washwashed with diethyl ether (3×50 ml)
6. customthe combined organic phases were evaporated in vacuo
7. additionThe residue was suspended in a mixture of diethyl ether (200 ml) and 96% ethanol (80 ml) and undissolved solid
8. filtrationwas filtered off
9. washwashed with diethyl ether
10. customThe organic phase was evaporated in vacuo
11. customaffording a solid which
12. customwas crushed under water (200 ml)
13. filtrationfiltered off
14. washwashed with water (3×50 ml), diethyl ether (3×40 ml)
15. customdried in vacuo at 50° C.

ORD record

ord-5d84abdf0a9946c7bd38c9223d049150

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06043247