1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone → 2-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-N-ethyl-N-methylethanamine

Participants

Reaction Steps

A solution of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone (1.05 g, 3.37 mmol) in THF (10 mL) was cooled to 0° C. then treated with BH3 in THF (1M) (33.7 mL, 33.7 mmol). The clear solution was allowed to warm to room temperature and stirred at this temperature for 3 days. The mixture was cooled to 0° C. and treated with methanol (5 mL) dropwise with caution. After stirring for 15 minutes, the mixture was concentrated to dryness then dissolved in methanol (25 mL) and concentrated again. The residue was dissolved in 25 mL methanol and heated at reflux for 5 hours then stirred at room temperature overnight. The reaction was concentrated to dryness to give a light yellow residue. This residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/95% CH2Cl2 to give a colourless residue (0.89 g, 89%). 1H-NMR (CDCl3) δ 7.09 (dd, J=1.8, 6.6 Hz, 1H), 7.02-7.01 (m, 1H), 6.44 (d, J=6.6 Hz, 1H), 3.36 (t, J=5.7 Hz, 2H), 3.29 (t, J=4.2 Hz, 2H), 2.70 (t, J=4.8 Hz, 2H), 2.53-2.43 (m, 4H), 2.28 (s, 3H), 1.94-1.88 (m, 2H), 1.06 (t, J=5.4 Hz, 3H). MS (ESI): 397.1 and 399.1 (M+1, 100%).

Provenance & Evidence