Reaction #2446127

Reaction equation

5-chloromethyl-8-hydroxyquinoline hydrochloride

diisopropylethylamine

ethyl 1-piperazinecarboxylate

→

title compound

Yield 42.0%

ethyl 4-(8-hydroxyquinolin-5-ylmethyl)-1-piperazine carboxylate

Yield 42.0%

Solvents

CHCl3

CHCl3

Conditions

Workup

1. 1
   Washthe solution was washed with 5% NaHCO3 (3×50 ml), brine (2×50 ml)
2. 2
   Dryingdried over Na2SO4
3. 3
   FiltrationThe solution was filtered
4. 4
   Otherevaporated to dryness
5. 5
   OtherThe residue was crystallized from a mixture of benzene-hexane (1:1)

Procedure

To a mixture of 5-chloromethyl-8-hydroxyquinoline hydrochloride (A2) (2.36 g, 10.2 mmol) and diisopropylethylamine (3.6 ml, 20.4 mmol, 2 eq) in 50 ml CHCl3 at 0° C., ethyl 1-piperazinecarboxylate (1.5 ml, 10.2 mmol, 1 eq) was added. The mixture was stirred for 24 h at room temperature, and then 100 ml of CHCl3 was added and the solution was washed with 5% NaHCO3 (3×50 ml), brine (2×50 ml), and then dried over Na2SO4. The solution was filtered and evaporated to dryness. The residue was crystallized from a mixture of benzene-hexane (1:1) to yield the title compound HLA16 as white solid. (1.38 g, 42% yield, m.p.=92-93° C.). H1 NMR (250 MHz, CDCl3), 1.25 (dd, J=7.1, 7.1 Hz 3H), 2.42 (s, 4H), 3.43 (s, 4H), 3.81 (s, 2H), 4.14 (dd, j=14.21, 7.12 Hz, 2H), 7.08 (d, J=7.72 Hz, 1H), 7.31 (m, 1H), 7.47 (dd, J=8.52, 4.20 Hz, 1H), 8.66 (dd, J=8.56, 1.58 Hz, 1H), 8.79 (dd, J=4.18. 1.54 Hz, 1H).

Source