Reaktion #93499

Reaktionsgleichung

3-[3(R)-ethenyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol dihydrochloride

sodium hydroxide

formaldehyde

sodium hydroxide

toluene-methanol diethylamine

→

desired product

3-[3(S)-ETHYL 4(R)-PIPERIDYL]-1-(6-METHOXY-4-QUINOLYL)-1(S)-PROPANOL

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Extraktionextracted with methylene chloride
3. 3
   WaschenThe organic phase was washed with water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Sonstigeevaporated under reduced pressure
6. 6
   SonstigeThe oily residue obtained

Vorschrift

A mixture of 6 g of 3-[3(R)-ethenyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol dihydrochloride, 15 ml of a normal aqueous solution of sodium hydroxide, 1.2 ml of a 0.4% aqueous solution of formaldehyde and 60 ml of water was heated at 120° C. for 24 hours in an autoclave. After cooling, the reaction medium was made alkaline by addition of sodium hydroxide lye and extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue obtained was subjected to high pressure liquid chromatography (support: silica gel; eluant: 100/7.5/3.75 toluene-methanol-diethylamine mixture). The separated fractions containing the desired product were evaporated. There was thus recovered 2.6 g of an oil which, by the action of HCl in ethanol, was converted into the dihydrochloride. After three recrystallizations of this last product in ethanol, 0.7 g of 3-[3(S)-ethenyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol were obtained in the form of the dihydrochloride melting at 204° C.

Quelle