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

HRID 1816750노트

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HRID 1816750 반응식
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

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 6415002,6-Dimethylmorpholine, cis-HCID 22494772Trifluoromethanesulfonic acid 4-(4-acetylpiperazin-1-yl)phenyl ester

생성물 1

HCID 540805081-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]ethanone

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2d61acc017724fe8bd01341a3c90d68a
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884868B1

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