Triethylamine → 4-(3-(3-methylpyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide

Participants

Reaction Steps

3-Methyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine hydrochloride (500 mg, 1.42 mmol, from Step 5), phenyl pyridin-3-ylcarbamate (333 mg, 1.56 mmol) and triethylamine (0.79 mL, 5.66 mmol) were combined in acetonitrile (10 mL) and stirred at room temperature. After 16 h, the reaction was concentrated forming a residue and the residue was partitioned between EtOAc and water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (0-5%, (8:1 EtOH:conc. NH4OH):CH2Cl2) to afford the title compound (445 mg) as a foamy white solid. MS (APCI 10V) AP+ 401.4, 281.2; 1H NMR (400 MHz, CD3OD) δ ppm 2.33 (s, 3H) 2.44 (td, J=5.81, 1.29 Hz, 2H) 2.57 (td, J=5.92, 1.22 Hz, 2H) 3.50-3.57 (m, 2H) 3.61-3.68 (m, 2H) 6.44 (s, 1H) 6.83-6.94 (m, 2H) 7.00-7.09 (m, 2H) 7.28-7.41 (m, 2H) 7.64-7.74 (m, J=7.28, 2.03, 1.07, 1.07 Hz, 1H) 7.87-7.96 (m, 2H) 8.16 (dd, J=4.80, 1.44 Hz, 1H) 8.58 (dd, J=2.60, 0.72 Hz, 1H).

Provenance & Evidence