Potassium Hydroxide → 3-(1,4'-Bipiperidin-1'-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Participants

Reaction Steps

Potassium hydroxide (1.86 g, 33.1 mmol) was added to a solution of methyl 3-(1,4′-bipiperidin-1′-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.1 g, 3.31 mmol) in methanol (60 mL) and water (20 mL). The mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and diluted with water. The methanol was removed in vacuo. The solid precipitate was collected by filtration, washed with cold water, and air dried to afford 3-(1,4′-bipiperidin-1′-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (2.0 g, 92% yield) as the potassium salt. 1H NMR (400 MHz, DMSO-d6) δ 8.52 (s, 1H), 8.11 (s, 1H), 7.91 (d, J=7.78 Hz, 1H), 7.79 (d, J=7.78 Hz, 1H), 7.67 (t, J=7.78 Hz, 1H), 7.55 (s, 1H), 4.04 (s, 3H), 3.42-3.52 (m, 4H), 2.33 (br. s., 4H), 2.03 (t, J=11.80 Hz, 1H), 1.82 (t, J=11.29 Hz, 2H), 1.39-1.48 (m, 6H), 1.30-1.39 (m, 2H), 1.12 (t, J=7.40 Hz, 3H), 0.97-1.09 (m, 2H); MS (m/z) 620.2 (M+H+).

Provenance & Evidence