Quipazine

2-(1-piperazinyl)quinoline is a member of pyridines and a member of piperazines.|Quipazine is a piperazine-based nonselective serotonin (5-HT) receptor agonist with antidepressant and oxytocic activities. Quipazine targets and binds to serotonin receptors, particularly to the 5HT2A and 5HT3 receptors. Serotonin receptor activation by quipazine may lead to smooth muscle contraction and antidepressant effects.|A pharmacologic congener of serotonin that contracts smooth muscle and has actions similar to those of tricyclic antidepressants. It has been proposed as an oxytocic.

To a solution formed by dissolving 4.31 g of anhydrous piperazine in 30 ml of ethylene glycol, 818 mg of 2-chloroquinoline was added, and stirred at 140°C for 2 hours. After cooling, saturated aqueous sodium hydrogencarbonate solution was added, and the system was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (chloroform: methanol = 2:1) to provide 1.09 g (100percent) of 2-piperazin-1-ylquinoline. A mixture of 2-chloroquinoline (2 g; 0.0122 mole ; 1EQ) and piperazine (10.5 g; 0.122 mole ; 10 eq. ) in DMSO (5 ml) was refluxed for 2h. The reaction mixture was cooled to RT, diluted with H20 (20 mi) and extracted with DCM (3X20ML). The organic phases were combined, dried (NA2SO4) and concentrated in vacuo. The crude product was purified by SPE cartridge (Si, 10G), ELUTING with a gradient of 0 to 1percent of MeOH in DCM affording the title compound (1.42 g; yield 55percent). MS; (ES) m/z: 214.3 [MH+]. C13H15N3 requires 213.28. 'H NMR (300MHZ, CDCI3) 5 : 7.85 (d, 1H), 7.74 (d, 1H), 7.97-7. 45 (t/d, 2H), 7.2 (t, 1 H), 6.9 (d, 1H), 3.67 (t, 4H), 2.98 (t, 4H).A mixture of 2-chloroquinoline (2.0 g, 0.012 mol) and piperazine(2.1 g 0.024 mol) in toluene (15 mL) was refluxed stirring for 6 h.The reaction mixture was placed in an ice bath, diluted with 15 mLof water, acidified with concentrated HCl and filtrated. 40 mL ofwater was added to the filtrate and organic phase was separated.The aqueous phase was washed with ethyl ether and alkalized withsolid NaOH. The solid free base was separated by filtration andcrystallized from the mixture of ethanol and water to give compound(7).The title compound was isolated as a white powder. Yield: 52.2percent1.361 g, m.p. 81e84 C (lit. 81e83 C [23]).Step l0.20 g (2.45 mmol) of piperazine was dissolved in 15 mL of isopropanol in a dried round flask provided with nitrogen gas, 2-chloroquinoline 0.20 g (1.2 mmol) was added thereto, and the mixture was refluxed with stirring for 24 hrs. After adding water thereto, the reaction was extracted with ethyl acetate. The formed organic layer was washed with a saturated NaCl solution, dried over anhydrous magnesium sulfate,

antineoplastic

Molecular Weight:213.28
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:213.126597491
Monoisotopic Mass:213.126597491
Topological Polar Surface Area:28.2
Heavy Atom Count:16
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes