Piperidine → Ethyl 4-(piperidin-1-yl)benzoate

Temperature

80 °C

In a 250 mL round-bottomed flask was ethyl 4-bromobenzoate (816 µl, 5 mmol), piperidine (593 µl, 6.00 mmol), and CESIUM CARBONATE (2444 mg, 7.50 mmol) in dioxane (2.36E+04 µl) to give a white suspension. The solution was degassed with N2 (g) for 15 min and then added BINAP (156 mg, 0.25 mmol) and PALLADIUM(II) ACETATE (56.1 mg, 0.25 mmol). The reaction was heated to 100 °C and stirred under a reflux condenser overnight. The reaction was checked by LC-MS (complete), filtered, rinsed with DCM, concentrated in vacuo and onto silica gel. Purification by Iscos (25 g.) using 100% hexanes -> 40% EtOAc in Hexanes afforded a white solid. 950 mg of a white solid obtained. 1H NMR (300 MHz, DMSO- _d_ 6) d ppm 1.28 (t, _J_ =7.08 Hz, 3 H) 1.58 (s, 6 H) 3.31 - 3.38 (m, 4 H) 4.23 (q, _J_ =7.11 Hz, 2 H) 6.94 (m, _J_ =9.06 Hz, 2 H) 7.76 (m, _J_ =9.25 Hz, 2 H) LC-MS: Rt = 2.98 min. Method: Short Purity. MS ES+: 234.2 [M+H]+.

ORD record

ord-856e3e504ed54d0cb8cb9c559a0474c7

Source dataset

750 AstraZeneca ELN dataset

Original link

View source