Réaction #2446126

Équation de réaction

5-chloromethyl-8-hydroxyquinoline hydrochloride

diisopropylethylamine

N-propargylpiperazine

→

title compound

Rendement 86.0%

5-(4-propargylpiperazin-1-ylmethyl)-8-hydroxyquinoline

Rendement 86.0%

Solvants

CHCl3

CHCl3

Conditions de réaction

Traitement

1. 1
   Lavagethe solution was washed with 5% NaHCO3 (3×50 ml), brine (2×50 ml)
2. 2
   Séchagedried over Na2SO4
3. 3
   AutreThe crude product was purified by FC

Mode opératoire

To a mixture of 5-chloromethyl-8-hydroxyquinoline hydrochloride (A2) (323 mg, 1.407 mmol) and diisopropylethylamine (0.26 ml, 1.477 mmol, 1.05 eq) in 6 ml CHCl3 at 0° C., N-propargylpiperazine obtained in step 2(iii) above was added (173 mg, 1.407 mmol, 1 eq). The mixture was stirred for 24 h at room temperature. 10 ml of CHCl3 was then added and the solution was washed with 5% NaHCO3 (3×50 ml), brine (2×50 ml), and then dried over Na2SO4. The crude product was purified by FC to give the title compound (HLA20) as a white solid. (337 mg, 86% yield). H1 NMR (250 MHz, CDCl3), 2.23 (m, 1H), 2.54 (s, 8H), 3.28 (d, J=2.44 Hz, 2H), 3.80 (s, 2H), 7.08 (m, 1H), 7.36 (d, J=10.59, 1H), 7.46 (dd, J=8.55, 4.18 Hz, 1H), 8.67 (dd, J=8.56, 1.55 Hz, 1H), 8.78 (dd, J=4.18. 1.51 Hz, 1H); 13C NMR (100 MHz, CDCl3) 46.77, 51.98, 52.87, 60.55, 73.05, 78.92, 108.60, 121.40, 124.58, 127.87, 128.87, 134.10, 138.68, 147.50, 151.78.

Source