Reacción #2175494

Ecuación de reacción

2-Chloro-1-methylpyridinium iodide

(S)-(−)-3-Aminoquinuclidine dihydrochloride

4-Butylbenzoic acid

Triethylamine

→

(S)-4-butyl-N-(quinuclidin-3-yl)benzamide

Rendimiento 95.0%

Disolventes

water

Acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas subsequently injected into a Preparative HPLC instrument for purification
2. 2
   Concentraciónconcentrated under vacuum

Procedimiento

1.5 ml of Acetonitrile and Triethylamine (700 uL, 5.0 mmol) was added to a flask charged with (S)-(−)-3-Aminoquinuclidine dihydrochloride (199 mg, 1.0 mmol) and 4-Butylbenzoic acid (196 mg, 1.1 mmol), followed by addition of 2-Chloro-1-methylpyridinium iodide (383 mg, 1.5 mmol) at room temperature. After stirring overnight, about 2 ml of water was added to reaction mixture to resolve a clear solution that was subsequently injected into a Preparative HPLC instrument for purification. Desired fractions were combined and concentrated under vacuum. (S)-4-butyl-N-(quinuclidin-3-yl)benzamide (272 mg, 95% yield) was isolated as an oil. 1H NMR (400 MHz, Methanol-D4) δ (ppm): 8.24 (d, J=8.2 Hz, 2H), 8.41 (d, J=8.4 Hz, 2H), 4.42 (m, 1H), 3.84 (ddd, J=11.7, 9.9, 2.6 Hz, 1H), 3.35 (m, 4H), 2.69 (t, J=7.7 Hz, 2H), 2.36 (q, J=3.1 Hz, 1H), 2.24 (m, 1H), 2.10 (m, 2H), 1.94 (m, 1H), 1.62 (q, J=7.6 Hz, 2H), 1.37 (q, J=7.4 Hz, 2H), 0.95 (t, J=7.4 Hz, 3H). LCMS (ESI): m/z 287.1 (M+H [C18H26N2O]=287.20).

Fuente