2,4-Dimethoxybenzoic acid → HCID 45381408, compound

Participants

Reaction Steps

4.0 ml of DMF, N,N′-Diisopropylethylamine (5.6 ml, 32.14 mmol), and 2,4-Dimethoxybenzoic acid (1.75 g, 9.64 mmol) was added to a flask charged with (S)-(−)-3-Aminoquinuclidine dihydrochloride (1.60 g, 8.03 mmol) and stirred ice-water bath under nitrogen atmosphere. To the mixture was added 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium (3.05 g, 8.03 mmol) then mixture temperature was raised to ambient temperature slowly by removing the ice-water bath for 60 minutes. Reaction mixture was worked up by addition of 1N sodium hydroxide aqueous solution and extracted twice with ethyl acetate, combined organic layer was washed with saturated brine solution, dried over sodium sulfate, filtered, and concentrated to crude clear oil. Purification via preparative HPLC to obtain pure product of (S)-2,4-dimethoxy-N-(quinuclidin-3-yl)benzamide, (1.95 g, 84% yield) 1H NMR (400 MHz, Methanol-D4) δ (ppm): 7.42 (m, 1H), 7.11 (s, 2H), 4.45 (m, 1H), 3.95 (s, 3H), 3.83 (m, 1H), 3.80 (s, 3H), 3.39-3.27 (m, 5H), 2.37 (m, 1H), 2.19 (m, 1H), 2.11 (m, 2H), 2.01 (m, 1H). C16H22N2O3 =290.16 LCMS (M+H): m/z 291

Provenance & Evidence