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

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence