Reaktion #45688

Reaktionsgleichung

7-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

solid

Ausbeute 44.3%

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile

Ausbeute 44.3%

Lösungsmittel

dimethyl sulfoxide

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water and saturated brine
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   SonstigeThe solvent was evaporated away under reduced pressure
4. 4
   Sonstigethe resulting residue was purified by silica gel column chromatography (silica gel 10 g, dichloromethane:methanol=30:1)
5. 5
   workup.ADDITIONisopropyl ether was added
6. 6
   Filtrationthe insoluble matter was collected by filtration

Vorschrift

7-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile (I-136) (0.21 g, 0.63 mmol) was suspended in dimethyl sulfoxide (5 ml), then triethylamine (0.91 ml, 1.37 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.16 ml, 1.26 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (silica gel 10 g, dichloromethane:methanol=30:1) and preparative thin-layer chromatography (dichloromethane:methanol=20:1), then isopropyl ether was added, and the insoluble matter was collected by filtration to obtain a beige solid (0.12 g, 44%).

Quelle