Reaktion #1992597

Reaktionsgleichung

tryptamine

(±)-ethyl 2-benzoyl-5-chloro-valerate

chlorobenzene

→

title compound

Ethyl 2-phenyl-1-[2-(3-indolyl)-ethyl]-1,4,5,6-tetrahydronicotinate

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeformed
2. 2
   workup.DISTILLATIONto distill off slowly together with chlorobenzene
3. 3
   TemperaturAfter cooling the precipitate
4. 4
   Filtrationis filtered off
5. 5
   Waschenwashed with chlorobenzene
6. 6
   Sonstigethe combined chlorobenzene solution is evaporated from a bath of 40° C. on a rotating evaporator

Vorschrift

0.273 g. (0.0017 mole) of tryptamine are added to a solution of 0.229 g. (0.00085 mole) of (±)-ethyl 2-benzoyl-5-chloro-valerate prepared according to Example 29 in 5 ml. of chlorobenzene, and the reaction mixture is heated on an oil bath of 150° C. for 5 hours, with stirring, while the water formed is allowed to distill off slowly together with chlorobenzene. After cooling the precipitate is filtered off, washed with chlorobenzene, and the combined chlorobenzene solution is evaporated from a bath of 40° C. on a rotating evaporator. The title compound is obtained by subjecting the residue to column chromatography on 40 g. of silica gel (Geduran Si 60, 0.063-0.200 mm.) using toluene containing 10% of diethyl amine as an eluting agent.

Quelle