Phenylacetaldehyde → 3-[4-(Phenethyl-amino)-phenyl]-propionic acid ethyl ester

Participants

Reaction Steps

Tetramethylammonium triacetoxyborohydride (4.9 g, 18.6 mmol) was added to a solution of 3-(4-aminophenyl)-propionic acid ethyl ester (3.0 g, 15.5 mmol) and phenylacetaldehyde (1.08 mL, 15.5 mmol) in 1,2-dichloroethane (50 mL). The resultant solution was stirred at room temperature for ten minutes, then heated at reflux overnight. The solution was treated with a 1:1 solution of water:ammonium hydroxide. The organic layer was applied to a silica gel column and eluted with ethyl acetate/hexane ( 1/9) to give the product as an oil, 1.3 g (28%). MS: m/z 298 (MH+). 1H NMR (CDCl3): δ 1.24 (t, 3 H), 2.58 (t, 2 H), 2.86 (s, 3 H), 3.53 (t, 2 H), 3.67 (t, 2 H), 4.13 (q, 2 H), 4.32 (t, 2 H), 6.67 (d, 2 H), 7.09 (d, 2 H), 7.19-7.32 (m, 5 H).

Provenance & Evidence