N-Methylaniline → N-(3-bromopropyl)-N-methylaniline

Participants

Reaction Conditions

Reaction Steps

N-methylaniline (300 mg, 2.80 mmol), 1,3-dibromopropane (0.568 mL, 5.6 mmol), K2CO3 (1.16 g, 8.40 mmol) and 18-crown-6 (49.8 mg, 0.30 mmol) were dissolved in 20 mL of anhydrous DMF and mixture stirred for 24 hours at 35° C. The reaction mixture was filtered and washed with DCM, and filtrate dissolved in DCM (100 mL) before extraction in water. The organic layer was washed with water (2×50 ml), brine (50 ml), and dried over Na2SO4, followed by evaporation of solvents under reduced pressure and the residue purified by silica gel column chromatography (EtOAc:n-hexane 1:20 to 1:10) to obtain compound 14. Yield: 0.260 g (74%). 1H NMR (500 MHz, CDCl3): δ 2.16 (tt, 2H, J=6.5 and 13.5 Hz, Hc), 2.99 (s, 3H, NCH3, Ha), 3.46-3.55 (m, 4H, Hb and Hd), 6.71-6.79 (m, 2H, He and Hg), 7.24-7.29 (m, 2H, Hf). EI-MS: [M+H]+ C10H15BrN calcd 228.03, obsd 228.04.

Provenance & Evidence