Benzylamine → N-Benzyl-4-methoxyaniline

Participants

Reaction Conditions

Reaction Steps

Following general procedure D, a mixture of 4-chloroanisole (1.23 mL, 10 mmol), benzylamine (1.52 mL, 14 mmol), NaOt-Bu (1.15 g, 12 mmol), 10 (4 mg, 0.05 mol %), 1 (2.5 mg, 0.05 mol %), and Bu2O (3 mL) was heated to 85° C. for 1 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-50% EtOAc/hexanes) to provide the title compound as a yellow oil (2.059 g, 97%). 1H NMR (300 MHz, CDCl3) δ: 7.63-7.52 (m, 5H), 7.06 (d, J=9.0 Hz, 2H), 6.81 (d, J=9.0 Hz, 2H), 4.46 (s, 2H), 4.05 (s, 1H), 3.92 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 152.6, 143.1, 140.5, 129.2, 128.1, 127.7, 115.4, 114.6, 56.1, 49.5 ppm. IR (neat, cm−1): 3414, 3029, 2832, 1513, 1453, 1235, 1036, 820, 743, 698. Anal. Calcd. for C14H15NO: C, 78.84; H, 7.09. Found: C, 78.61; H, 7.10.

Provenance & Evidence