Potassium Carbonate → Ethyl 4-(4-hydroxypiperidin-1-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

In a 200 mL round bottom flask, piperidin-4-ol (2.165 g, 21.41 mmol) and K2CO3 (2.96 g, 21.41 mmol) were suspended in MeCN (51.0 mL). Ethyl 4-fluorobenzoate (2.62 mL, 17.84 mmol) was added and the reaction mixture was stirred under reflux (95° C.) for 96 hr. The reaction was cooled to RT, diluted with EtOAc (100 mL) and washed with water (50 mL). Dried organic layer with MgSO4, filtered, and concentrated in vacuo. The product was purified by re-crystallization using EtOAc/hexanes, affording the title compound as a white solid (0.878 g, 19.74% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (t, J=7.07 Hz, 3H) 1.34-1.47 (m, 2H) 1.73-1.85 (m, 2H) 3.03 (ddd, J=13.14, 9.98, 3.16 Hz, 2H) 3.63-3.77 (m, 3H) 4.23 (q, J=7.07 Hz, 2H) 4.72 (d, J=4.04 Hz, 1H) 6.86-7.05 (m, 2H) 7.66-7.85 (m, 2H). ESI-MS: m/z 250.2 (M+H)+.

Provenance & Evidence