Toluene → HCID 86695293, compound

Participants

Reaction Conditions

Reaction Steps

68.95 g (0.333 mol) of 1-(2-fluorobenzyl)-4-piperidone crude product was added to a reaction bottle, and 290 mL of toluene was added. The reaction heated at 80° C. in an oil bath under stirring, and then to the reaction 83.00 g (0.377 mol) of trimethylsulfoxide iodide and 2.20 g (0.0065 mol) of tetrabutylammonium hydrogen sulfate was added in sequence. Then to the reaction 28.40 g (0.710 mol) sodium hydroxide dissolved in 90 mL of aqueous solution was added dropwise under stirring. After the addition, the reaction was stirred at 80° C. of bath temperature overnight. On the next day, the reaction was cooled, washed with water twice, extracted with a small amount of toluene, combined, and the solvent was recovered to obtain light yellow liquid, 54.70 g (74.2%), i.e., a crude target product. 1H-NMR (CDCl3, ppm) δ: 7.394 (1H, dt, J1=7.56 Hz, J2=1.68 Hz), 7.254 (1H, m), 7.118 (1H, ddd, J1=7.56 Hz, J2=1.12 Hz), 7.037 (1H, dtd, J1=8.96 Hz, J2=1.12 Hz), 3.562 (2H, d, J=1.12 Hz), 2.647 (2H, s), 2.637 (4H, m), 1.820 (2H, m), 1.569 (2H, m).

Provenance & Evidence