Reaktion #66143

Reaktionsgleichung

sodium hydroxide

{2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl}-methanol

4-(3-chloro-propyl)-morpholine

→

4-(3-{2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-benzyloxy}-propyl)-morpholine

Ausbeute 80.2%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux
3. 3
   Temperaturreflux
4. 4
   workup.WAITcontinued for 28 h
5. 5
   TemperaturThe reaction mixture was cooled
6. 6
   Sonstigethe organic phase separated
7. 7
   ExtraktionThe aqueous phase was extracted with ethyl acetate (3×5 mL)
8. 8
   Waschenwashed with water and brine
9. 9
   Trocknendried over anhydrous sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated under vacuum
12. 12
    Sonstigeto give a residue which
13. 13
    Sonstigewas purified by preparative TLC
14. 14
    Wascheneluting with 2% methanol in chloroform

Vorschrift

Aqueous sodium hydroxide (50% w/w, 10 g, 125 mmol) and tetrabutylammonium hydrogen sulfate (0.20 g) were added successively to a solution of {2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl}-methanol (0.50 g, 1.46 mmol) in toluene (5 mL). The mixture was heated to reflux with vigorous stirring for 45 min then 4-(3-chloro-propyl)-morpholine (0.50 g, 3.00 mmol) was added and reflux continued for 28 h. The reaction mixture was cooled and the organic phase separated. The aqueous phase was extracted with ethyl acetate (3×5 mL). The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give a residue which was purified by preparative TLC eluting with 2% methanol in chloroform to afford 4-(3-{2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-benzyloxy}-propyl)-morpholine (550 mg, 80%) as a solid.

Quelle