4-Methylmorpholine → Tert-butyl 4-(4-(ethylcarbamoyl)-2-methylphenyl)piperazine-1-carboxylate

Participants

Reaction Steps

4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-methylbenzoic acid 294 (0.866 g, 2.70 mmol), ethanamine hydrochloride (0.264 g, 3.24 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.777 g, 4.05 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol hydrate (0.621 g, 4.05 mmol) were suspended in DMF (3.68 mL) and 4-methylmorpholine (1.486 mL, 13.52 mmol) was added. The reaction mixture was stirred at ambient temperature for 2 h, diluted with water (50 mL), and extracted with ethyl acetate (3×75 mL). The combined organic extracts were washed with 1N HCl(aq., 25 mL), NaHCO3 (sat. aq., 25 mL), water (25 mL), and brine (25 mL), dried over MgSO4, concentrated in vacuo, and dried under vacuum to afford the title compound as a white solid (0.9327 g, 2.68 mmol, 99% yield). 1H NMR (DMSO-d6, 400 MHz): δ=8.24 (t, J=5.4 Hz, 1H), 7.66 (d, J=1.8 Hz, 2H), 7.03 (d, J=8.3 Hz, 1H), 3.42-3.52 (m, 4H), 3.20-3.27 (m, 2H), 2.78-2.87 (m, 4H), 2.28 (s, 3H), 1.43 (s, 9H), 1.10 ppm (t, J=7.2 Hz, 3H). ESI-MS: m/z 348.4 (M+H)+.

Provenance & Evidence