Triethylamine → HCID 57961674, compound

Participants

Reaction Steps

To a stirring solution of tert-butyl [3-(aminomethyl)phenyl]carbamate (2.0 g, 9.0 mmol) and triethylamine (1.3 mL, 9.4 mmol) in dry tetrahydrofuran (25 mL) at 0° C. slowly added a solution of 3-nitrobenzoyl chloride (1.75 g, 9.45 mmol) in tetrahydrofuran (7.3 mL). The resulting mixture was slowly warmed up to rt and stirred for one additional hour at rt. The reaction mixture was treated with Na2CO3 (aq), separated. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the desired product as an off-white powder (3.5 g, 100%). LCMS for C19H21N3O5 (M-tBu+H)+: m/z=316.0. 1H NMR (400 MHz, CD3OD): δ 8.71 (t, J=2.0 Hz, 1H), 8.38 (ddd, J=8.4, 1.6, 1.2 Hz, 1H), 8.23 (ddd, J=8.0, 1.6, 0.8 Hz, 1H), 7.70 (t, J=8.0 Hz, 1H), 7.44 (s, 1H), 7.28 (m, 1H), 7.20 (t, J=7.6, 1H), 7.00 (d J=7.6 Hz, 1H), 4.90 (s, 2H), 1.49 (s, 9H).

Provenance & Evidence