N,N-Dimethylethylenediamine → 3-(3,4-dihydroquinolin-1(2H)-yl)-N-(2-(dimethylamino)ethyl) propanamide

Participants

Reaction Steps

To a solution of Compound 7 (1.0 g, 4.9 mmol) in DMF (20 mL), 2-succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate (1.8 g, 5.8 mmol) and N,N-diisopropyl ethylamine (1.8 mL, 10.2 mmol) were added. Combined mixture was stirred at room temperature for 30 mins and then a solution of N,N-dimethylethylenediamine (0.64 g, 7.3 mmol) in DMF (2 mL) was added. After stirring the mixture for additional 1 hour, it was poured in brine (100 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers were washed with brine (3×100 mL) and dried over MgSO4. The solvent was removed under reduced pressure to provide Compound 8 as brown viscous liquid (0.74 g, 55%). This product was used without further purification. The structure of Compound 8 is given below:

Provenance & Evidence