Reacción #2175504

Ecuación de reacción

sodium hydroxide

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

4-Iodobenzoyl chloride

N,N′-Diisopropylethylamine

→

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

Rendimiento 64.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted twice with ethyl acetate
2. 2
   Lavadowas washed with saturated brine solution
3. 3
   Secadodried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated to crude clear oil
6. 6
   OtroThe crude oil was purified via preparative HPLC

Procedimiento

N,N′-Diisopropylethylamine (1.05 ml, 6.03 mmol) was added to a flask charged with DMF solution mixture of (S)-(−)-3-Aminoquinuclidine dihydrochloride (400 mg, 2.01 mmol) and 4-Iodobenzoyl chloride (616 mg, 2.31 mmol). The clear yellow solution was stirred for 3 hours. The 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. The crude oil was purified via preparative HPLC to obtain pure product of (S)-4-iodo-N-(quinuclidin-3-yl)benzamide, (460 mg, 64% yield). 1H NMR (400 MHz, Methanol-D4) δ (ppm): 7.85 (d, J=8 Hz, 2H), 7.60 (d, J=8 Hz, 2H), 4.12 (m, 1H), 3.31 (m, 1H), 2.99 (m, 1H), 2.84 (m, 4H), 2.02 (m, 1H), 1.90 (m, 1H), 1.78 (m, 2H), 1.54 (m, 1H). C14H17IN2O=356.04 LCMS (M+H): m/z 357

Fuente