Synthesis
General procedure for the synthesis of N-methyl-2-naphthalenemethylamine from 2-bromomethylnaphthalene: 2-bromomethylnaphthalene (10 g, 43 mmol) was added batchwise to a stirred mixture of 40 wt% aqueous methylamine solution (50 mL, 581 mmol) and THF (50 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was concentrated under vacuum. The concentrated residue was dissolved in ether (Et2O), washed sequentially with 1.0 N NaOH solution and brine, and the organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated to dryness. Purification by silica gel fast column chromatography (eluent ratio from 98:2 to 9:1 CHCl3/methanol containing 5% NH4OH) afforded N-methyl-2-naphthalenemethylamine (3.95 g, 54% yield) as a clear oil. Its 1H NMR (400 MHz, CDCl3) data were as follows: δ 7.85 (m, 3H), 7.79 (s, 1H), 7.49 (m, 3H), 3.94 (s, 2H), 2.53 (s, 3H).
