Benzaldehyde → 4-(2-(Benzylamino)ethyl)phenol

Participants

Reaction Conditions

Reaction Steps

Combine tyramine (5 g, 36.5 mmol), benzaldehyde (9.9 g, 45.6 mmol), 3 Å molecular sieves (10 g), and methanol (200 mL) and stir overnight at room temperature. Cool to 5° C. then add sodium borohydride (5.5 g, 146 mmol) to the reaction. Stir for 2 hours then concentrate on a rotary evaporator. Dilute in methanol, filter, then concentrate on a rotary evaporator. The residue was taken up in 1N hydrochloric acid and washed with diethyl ether. The aqueous layer was basified then extracted with ethyl acetate (2×100 mL. The ethyl acetate extracts were combined, dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield 4-(2-Benzylamino-ethyl)-phenol (3.3 g) 1H NMR (CDCl3, 300.00 MHz): 9.14 (s, 1H), 7.35-7.20 (m, 5H), 7.01-6.96 (m, 2H), 6.69-6.64 (m, 2H), 5.19 (s, 1H), 3.73 (s, 2H), 2.72-2.60 (m, 4H).

Provenance & Evidence