1,4'-Bipiperidine → Methyl 3-(1,4'-bipiperidin-1'-ylmethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Participants

Reaction Steps

A suspension of methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.45 g, 2.88 mmol) and 1,4′-bipiperidine (0.630 g, 3.74 mmol) in acetonitrile (10 mL) was stirred for 3 hours. The solvent was removed under reduced pressure. The residue was dissolved in DMSO and was purified via HPLC (Biotage, 0-50% MeCN/H2O with 0.1% TFA). Fractions containing the product were neutralized with saturated aqueous NaHCO3 and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford methyl 3-(1,4′-bipiperidin-1′-ylmethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.47 g, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.43 (d, J=1.76 Hz, 1H), 8.37 (d, J=8.78 Hz, 1H), 8.27-8.33 (m, 1H), 8.00 (s, 1H), 7.89-7.96 (m, 2H), 7.76-7.82 (m, 1H), 4.04 (s, 3H), 3.66 (s, 2H), 3.39 (s, 3H), 2.54-2.71 (m, 3H), 2.31-2.47 (m, 4H), 1.82 (br. s., 2H), 1.53 (d, J=10.04 Hz, 2H), 1.45 (br. s., 4H), 1.21-1.40 (m, 4H); MS (m/z) 590.2 (M+H+).

Provenance & Evidence