반응 #93499

반응 방정식

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

용매

water

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   추출extracted with methylene chloride
3. 3
   세척The organic phase was washed with water
4. 4
   건조dried over magnesium sulfate
5. 5
   기타evaporated under reduced pressure
6. 6
   기타The oily residue obtained

실험 절차

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.

출처