Reaktion #351564

Reaktionsgleichung

DDQ

(S)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine

triethylamine

ethyl trifluoroacetate

→

(S)-N-[2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethyl]-trifluoracetamide

Ausbeute 59.0%

Lösungsmittel

dioxane

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturunder reflux for 1.5 hours
3. 3
   EinengenSubsequently, the reaction mixture was concentrated in a vacuum
4. 4
   Sonstigethe residue was purified by column chromatography on silica gel (dichloromethane/acetone 4:1)

Vorschrift

A solution of 1.5 g of (S)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine, 0.74 g of triethylamine and 1.04 g of ethyl trifluoroacetate in 100 ml of anhydrous methanol was stirred at room temperature for 27 hours. After the solvent had been drawn off in a vacuum, the residue was taken up with 100 ml of ahydrous dioxane, 1.56 g of DDQ were added and the mixture was boiled under reflux for 1.5 hours. Subsequently, the reaction mixture was concentrated in a vacuum and the residue was purified by column chromatography on silica gel (dichloromethane/acetone 4:1). 1.2 g (59%) of (S)-N-[2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethyl]-trifluoracetamide were obtained as a pale brown solid which was used in the next reaction without additional recrystallization.

Quelle