4-Chloroaniline → 4-chloro-N-(2-(diethylamino)ethyl)aniline

Participants

Reaction Steps

4-Chloro-aniline (0.5 g, 3.9 mmol) was added to a solution of 2-bromo-N,N-diethylethylamine hydrobromide (1.12 g, 4.3 mmol) and N,N-diisopropylethylamine (2 mL, 11.7 mmol) in toluene (7.8 mL). The mixture was stirred at room temperature for 5 hours. The mixture was then diluted with EtOAc (30 mL) and saturated NaHCO3 (20 mL). The organic layer was washed with H2O (1×20 mL), dried (Na2SO4), filtered and concentrated to give 4-chloro-N-(2-(diethylamino)ethyl)benzenamine as an oil which was used without purification. MS (APCI+) [M+H]+ 227.3.

Provenance & Evidence