68-12-2

86-52-2

16413-71-1

Sodium hydroxide (3.0 eq.), NHC-Pd(II)-Im complex 1 (1.0 mol%), water (1.0 mL), 1-chloromethylnaphthalene (0.8 mmol), and N,N-dimethylformamide (2.0 eq.) were sequentially added to the Schlenk reaction tube under nitrogen protection. The reaction mixture was stirred at 50 °C for 3 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was extracted with ethyl acetate, the extract was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting crude product was purified by rapid column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=5:1) to afford the pure N,N-dimethyl-1-(naphthalen-1-yl)methylamine (4t). The product was a colorless liquid with the following NMR hydrogen spectrum (300 MHz, CDCl3) data: δ 8.24 (d, J = 7.8 Hz, 1H), 7.83-7.75 (m, 2H), 7.51-7.36 (m, 4H), 3.79 (s, 2H), 2.27 (s, 6H); NMR carbon spectrum (75 MHz, CDCl3) data are as follows: δ 134.6, 133.8, 132.4, 128.4, 127.9, 127.4, 125.9, 125.5, 125.0, 124.4, 62.4, 45.6.