Triethylamine → 3-bromo-N-cyclopropyl-5-(3-methoxypropyl)-4-methylbenzamide

Participants

Reaction Steps

To a stirred solution of 3-bromo-N-cyclopropyl-5-(3-methoxy-prop-1-ynyl)-4-methyl-benzamide and platinum oxide (0.04 equiv.) in toluene (˜0.12 M) was added triethylamine (0.2 equiv.). The resultant solution was hydrogenated at 1.8 Barg for 3 h and then filtered to remove the catalyst. The solution was concentrated to ˜4 volumes and then heptane added (8 volumes). The resultant slurry was filtered to afford the product as an off-white solid. 1H NMR (500 MHz, Acetone-d6): δ 7.87 (m, 2 H), 7.65 (s, 1 H), 3.35 (t, J=6.12 Hz, 2 H), 3.27 (s, 3 H), 2.93-2.86 (m, 1 H), 2.75 (t, J=7.91 Hz, 2 H); 2.39 (s, 3 H), 1.80-1.72 (m, 2 H), 0.75-0.67 (m, 2 H), 0.61-0.56 (m, 2 H). HRMS (ES, M+H) Calcd 326.0767. Found 326.0756.

Provenance & Evidence