Potassium Carbonate → HCID 19788729, compound

Participants

Reaction Steps

A stirred solution of 4-[4-methylsulfonylaminobenzoyl)piperidine hydrochloride (2.25 g, 7.06 mmol), 2-[(4-(methylsulfonyamino)phenoxy)-methyl]oxirane (U.S. Pat. No. 4,994,459, 1.73 g, 7.06 mmol) and K2CO3 (0.98 g, 7.06 mmol) in ethanol (40 mL) was heated at 90° C. for 24 hours and then at 25° C. for an additional 24 hours. The mixture was concentrated and the residue was partitioned between aqueous 10% NaHCO3 and 4:1 CH2Cl2 /isopropanol. The organic phase was dried and concentrated to afford 2.89 g (78%) of the title compound. A portion (1.60 g) was purified by HPLC (15% CH3OH/EtOAc) to give 0.92 g of product as a white solid: mp 179°-183° C. (dec); 1H NMR (DMSO-d6): δ 10.20 (brs, 1H), 9.33 (brs, 1H), 7.94 (d, J=8.72 Hz, 2H), 7.26 (d, J=8.92 Hz, 2H), 7.13 (d, J=9.13 Hz, 2H), 6.91 (d, J=8.92 Hz, 2H), 4.83 (m,1H), 3.93 (m, 2H), 3.85 (m, 1H), 3.09 (s, 3H), 2.96 (m, 2H), 2.87 (s, 3H), 2.45 (m, 2H), 2.20 (m, 2H), 1.75-1.50 (m, 4H); IR (KBr): 3420, 3300, 3250, 2910, 1675, 1610 cm-1 ; MS (m/z) 526 (MH+, 25%), 217 (40), 91 (100).

Provenance & Evidence