Benzenesulfonamide → HCID 15491312, compound

Participants

Reaction Steps

In a round-bottomed flask fitted with a reflux condenser and a thermometer was introduced (2-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-ethoxy)-acetic acid (compound 235 prepared at example 1.4.2; 2.7 g, 4.54 mmoles) dissolved in CH2Cl2 (25 ml). Benzenesulphonamide (1.07 g, 6.8 mmoles), DMAP (10 mg, 0.45 mmoles) and EDCI (0.96 g, 5 mmoles) were added to the solution and the reaction mixture was stirred at room temperature for 48 hours. The organic solution was washed with HCl 0.1N and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/NH3: 95/5/0.2 v/v/v) to afford the monohydrate of N-[(2-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-ethoxy)-acetyl]-benzenesulfonamide (compound 306; 1.5 g, 50%) as a beige solid.

Provenance & Evidence