Acetic Acid → HCID 70874194, compound

Participants

Reaction Steps

To a stirred solution of ethyl 3-(benzylamino)-2-methylbenzoate (396 mg, 1.47 mmol) in DCE (10 ml) was added acetaldehyde (164 μl, 2.94 mmol) followed by acetic acid (0.17 ml, 2.94 mmol) The reaction was stirred at room temperature for 10 min and then sodium triacetoxyborohydride (0.62 g, 2.94 mmol) was added and the reaction stirred for 16 h. Distilled water (30 ml) was added and solid NaHCO3 was then added until the aqueous phase was pH7, the phases were separated, the aqueous phase was washed with DCM (2×50 ml), the combined organics were then washed with brine (50 ml), dried using Na2SO4, filtered and evaporated. The resultant residue was then purified using a 25 g silica Isolute column eluting using a gradient of 0% to 5% EtOAc in heptane to afford the title compound as a colourless oil (372 mg, 81%). LC-MS 94%, m/z=298.1, 1H NMR (500 MHz, Chloroform-d) δ 7.48 (dd, J=7.5, 1.3 Hz, 1H), 7.29-7.08 (m, 8H), 4.32 (q, J=7.1 Hz, 2H), 4.05 (s, 2H), 2.92 (q, J=7.1 Hz, 2H), 2.56 (s, 3H), 1.35 (t, J=7.1 Hz, 3H), 0.92 (t, J=7.1 Hz, 3H).

Provenance & Evidence