Piperidine → HCID 67529104, compound

Participants

Reaction Steps

To a stirred solution of methyl 4-bromo-3-methylbenzoate (ABCR, 5 g, 21.8 mmol) in dry 1,4-dioxane (100 mL), were added dry Cs2CO3 (10.65 g, 32.7 mmol) and piperidine (2.2 g, 26 mmol). The mixture was degassed with N2 for 10 min. BINAP (0.67 g, 1.1 mmol) and palladium(II)acetate (0.24 g, 1.1 mmol) were added under N2 and the resulting mixture was refluxed for 15 h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The crude product was purified by flash chromatography, affording the title product as a off-white solid (4.9 g, 96%). 1H NMR (CDCl3, 400 MHz) δ 7.82-7.84 (m, 2H), 6.97-6.99 (d, 1H), 3.92 (s, 3H), 2.90-2.93 (m, 4H), 1.67-1.76 (m, 4H), 1.62-1.63 (m, 2H). LC/MS (Method A): 233.9 (M+H)+. HPLC (Method B) Rt 4.18 min (Purity: 95.4%).

Provenance & Evidence