Reaktion #639005

Reaktionsgleichung

3-(pyrrolidin-3-yl)pyridine

triethylamine

phosgene

4-difluoromethylene-1,2,3,4-tetrahydroquinoline

→

(4-difluoromethylene-3,4-dihydro-2H-quinolin-1-yl)(3-(pyridin-3-yl)pyrrolidin-1-yl)methanone

Lösungsmittel

dichloromethane

toluene

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a magnetic stirrer
2. 2
   TemperaturAfter cooling to +4° C.
3. 3
   TemperaturThe reaction medium is cooled in an ice bath
4. 4
   workup.STIRRINGThe mixture is stirred at ambient temperature for 18 h
5. 5
   WaschenThe reaction medium is washed with a 1N sodium hydroxide solution
6. 6
   Trocknenthe organic phase is dried over sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue is chromatographed on silica gel
9. 9
   Wascheneluted with a dichloromethane/methanol 98/2 mixture

Vorschrift

0.07 g of 4-difluoromethylene-1,2,3,4-tetrahydroquinoline and 5 ml of dichloromethane are introduced into a three-necked flask equipped with a magnetic stirrer and placed under an inert atmosphere. After cooling to +4° C., 0.11 ml of triethylamine and 0.39 ml of a 20% solution of phosgene in toluene are successively added. The reaction medium is stirred at ambient temperature for 2 h. The reaction medium is cooled in an ice bath and 0.08 g of 3-(pyrrolidin-3-yl)pyridine in 2 ml of dichloromethane is then introduced. The mixture is stirred at ambient temperature for 18 h. The reaction medium is washed with a 1N sodium hydroxide solution; the organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel eluted with a dichloromethane/methanol 98/2 mixture. 0.05 g of (4-difluoromethylene-3,4-dihydro-2H-quinolin-1-yl)(3-(pyridin-3-yl)pyrrolidin-1-yl)methanone is obtained and is treated with fumaric acid in an ethanol/diisopropyl ether mixture to give the fumarate.

Quelle