Reaktion #68073

Reaktionsgleichung

ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylate

sodium hydroxide

→

4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylic acid

Ausbeute 30.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturrefluxed
3. 3
   Temperaturwith heating for 5 hours
4. 4
   Sonstigethe solvent was removed under reduced pressure, water
5. 5
   workup.ADDITIONwas added
6. 6
   SonstigeThe solvent was removed under reduced pressure
7. 7
   Sonstigethe residue thus obtained
8. 8
   Sonstigewas purified by reversed-phase silica gel column chromatography [eluent; acetonitrile:water=3:7]

Vorschrift

To 0.8 mL of an ethanol solution containing 80 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylate, 0.2 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 5 hours. After the reaction mixture was cooled to the room temperature, the solvent was removed under reduced pressure, water was added, and adjusted to pH 6.8 with 6.0 mol/L hydrochloric acid. The solvent was removed under reduced pressure, and the residue thus obtained was purified by reversed-phase silica gel column chromatography [eluent; acetonitrile:water=3:7] to give 23 mg of 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)-1-(3-phenylpropyl)piperidine-4-carboxylic acid as a white solid.

Quelle