Benzylamine → Benzyl-(3-methoxy-4-nitro-benzyl)amine

Participants

Reaction Steps

To a 150 mL round bottomed flask containing 1.97 g (8.0 mmol) of 3-methoxy-4-nitro-benzyl bromide in 20 mL THF was added, 2.4 g (24 mmol, 3eq.) of triethylamine followed by 2.5 g (24 mmol, 3 eq.) of benzylamine. The mixture was stirred at room temperature for 2 h, and was then partitioned between 50 mL ethyl acetate and brine. The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 1-4% MeOH in dichloromethane to give 1.6 g (73%) of the benzyl amine as a yellow oil. 1H NMR (400 MHz, CDCl3): δ7.84 (d, J=8.61 Hz, 1H), 7.34 (m, 5H), 7.16,(s, 1H), 6.99 (d,J=8.61 Hz, 1H), 3.97 (s, 3H), 3.86 (s, 2H), 3.81 (s, 2H).

Provenance & Evidence