Benzenesulfonic Acid → HCID 19772006, compound

Participants

Reaction Steps

A solution of 22.26 g (0.064 mol) of (4-fluorophenyl)[1-(phenylsulfonyl)-4-piperidinyl]methanone, 12.51 g (0.10 mol) of 4-fluorobenzylamine, and 0.76 g (0.0048 mol) of benzenesulfonic acid in 400 mL of xylene was heated at reflux for 25.5 h. Water was removed with a Dean-Stark trap. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (Na2SO4), and the solvent was removed in vacuo. The residue was recrystallized from CH2Cl2 -hexane to give 18.49 g (63.68%) of white crystalline solid, mp 114°-116° C. A second crop of 3.27 g (11.28%) of product was isolated from the filtrate as a white solid, mp 110°-112° C.

Provenance & Evidence