Cesium carbonate → 1-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]ethanone

HRID 1816750Notizen

Reaktionsgleichung

C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:53][C@H:54]1[O:59][C@@H:58]([CH3:60])[CH2:57][NH:56][CH2:55]1.[C:61]([N:64]1[CH2:69][CH2:68][N:67]([C:70]2[CH:75]=[CH:74][C:73](OS(C(F)(F)F)(=O)=O)=[CH:72][CH:71]=2)[CH2:66][CH2:65]1)(=[O:63])[CH3:62]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:60][C@H:58]1[O:59][C@@H:54]([CH3:53])[CH2:55][N:56]([C:73]2[CH:72]=[CH:71][C:70]([N:67]3[CH2:66][CH2:65][N:64]([C:61](=[O:63])[CH3:62])[CH2:69][CH2:68]3)=[CH:75][CH:74]=2)[CH2:57]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of cesium carbonate (25.32 g), palladium(II) acetate (0.624 g) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.59 g) in toluene (110 ml) was successively added cis-2,6-dimethylmorpholine (8.21 ml) and trifluoromethanesulfonic acid 4-(4-acetylpiperazin-1-yl)phenyl ester (20 g) in stream of nitrogen. The mixture was stirred at ambient temperature for 30 minutes and at 100° C. for further 12 hours. After cooling to room temperature, water was added to the reaction mixture. The resulting precipitates were filtered, washed with water and dried. The residue was purified by silica gel chromatography (50:1 dichloromethane-methanol elution) to give 1-[4-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]ethanone (7.78 g).

Aufarbeitung

temperatureAfter cooling to room temperature
customThe resulting precipitates
filtrationwere filtered
washwashed with water
customdried
customThe residue was purified by silica gel chromatography (50:1 dichloromethane-methanol elution)

Quellen und Nachweise

ORD-Eintrag: ord-2d61acc017724fe8bd01341a3c90d68a
Quelldatensatz: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06884868B1

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