Reaktion #449431

Reaktionsgleichung

(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one

4-(1H-indol-4-yl)-piperazine

→

title compound

Ausbeute 73.3%

2-[4-(1H-Indol-4-yl)-piperazin-1-ylmethyl]-2,3,8,9-tetrahydro-7H-1.4-dioxino[2.3-e]indol-8-one

Ausbeute 73.3%

Lösungsmittel

ethyl acetate hexane

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Waschenwashed with 400 ml of saturated sodium bicarbonate solution, with two 250 ml portions of water and with saturated brine
3. 3
   TrocknenThe mixture was dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuum
6. 6
   Sonstigeto yield an oil, which
7. 7
   Sonstigechromatographed on silica gel using 0.5% methanol/CHCl3 as eluant

Vorschrift

(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one (1.0 g, 2.7 mmole) and 4-(1H-indol-4-yl)-piperazine (2.0 g, 10 mmole) were combined in 30 ml of dry DMSO and heated to 80° C. for 4 hours under an argon atmosphere. After cooling to room temperature, the mixture was diluted with 400 ml of 1:1 ethyl acetate/hexane and washed with 400 ml of saturated sodium bicarbonate solution, with two 250 ml portions of water and with saturated brine. The mixture was dried over sodium sulfate, filtered and concentrated in vacuum to yield an oil, which was column chromatographed on silica gel using 0.5% methanol/CHCl3 as eluant. The free base of the title compound (0.80 g) thus obtained was crystallized from methanol with the addition of one equivalent of fumaric acid to give 077 g of the (S) enantiomer of the title compound as a white solid fumarate, m.p. 237°-238° C.

Quelle