N-Aminomorpholine → N-((8-chloro-2-(2-chlorophenyl)-quinolin-3-yl)methyl)morpholin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 8-chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline (Prepared in Example 2), N,N-diisopropylethylamine (0.584 mL, 3.35 mmol), and lithium iodide (0.00566 mL, 0.148 mmol) in 7 mL of DMF was added 4-aminomorpholine (0.0647 mL, 0.670 mmol) and the mixture was stirred at 50° C. After 19 h, the mixture was concentrated under reduced pressure to give an yellow oil. The crude mixture was purified by column chromatography on a 40 g of Redi-Sep™ column using 0-100% gradient of EtOAc in hexane over 14 min and then 100% isocratic of EtOAc for 10 min as eluent to give N-((8-chloro-2-(2-chlorophenyl)-quinolin-3-yl)methyl)morpholin-4-amine as a light yellow foam (syrup): 1H NMR (400 MHz, choroform-d) δ ppm 8.39 (1H, s), 7.73-7.88 (2H, m), 7.37-7.53 (5H, m), 3.78-4.07 (2H, m), 3.64 (4H, t, J=4.7 Hz), 2.53 (4H, s); LC-MS (ESI) m/z 388.0 and 390.1 [M+H]+.

Provenance & Evidence