Reaktion #88179

Reaktionsgleichung

water

Triethylamine

(R)-3-(2-ethoxy-phenoxy)-piperidine

ethyl 6-chloronicotinate

→

ethyl (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinate

Ausbeute 60.9%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to ambient temperature
2. 2
   Extraktionthe mixture was extracted with ethyl acetate (3×200 mL)
3. 3
   WaschenThe combined organic layers were washed sequentially with water (100 mL) and brine (100 mL)
4. 4
   Trocknenwere dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude material was purified by column chromatography (13% ethyl acetate-hexanes)

Vorschrift

Triethylamine (8.1 mL, 80 mmol) was added to a stirred solution of (R)-3-(2-ethoxy-phenoxy)-piperidine (10 g, 39 mmol) and ethyl 6-chloronicotinate (7.2 ml, 39 mmol) in acetonitrile (100 mL) at 0° C. The reaction mixture was heated at 90° C. for 16 h. The mixture was cooled to ambient temperature, water (150 mL) was added, and the mixture was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed sequentially with water (100 mL) and brine (100 mL), then were dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography (13% ethyl acetate-hexanes) to afford ethyl (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinate (8.8 g). MS (ES+) 371.0 (M+H).

Quelle