Cesium carbonate → 1-Acetyl-4-[4-(4-methoxy-4-phenylpiperidin-1-yl)phenyl]piperazine

HRID 1816740노트

반응식

HRID 1816740 반응식
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:24][O:25][C:26]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.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.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.ClCCl.[Pd+2].C([O-])(=O)C.C([O-])(=O)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:29]3[CH2:30][CH2:31][C:26]([O:25][CH3:24])([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:27][CH2:28]3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 417384HCID 417384, 화합물HCID 634876Binap, (A+-)-HCID 22494772Trifluoromethanesulfonic acid 4-(4-acetylpiperazin-1-yl)phenyl ester

생성물 1

HCID 224947141-Acetyl-4-[4-(4-methoxy-4-phenylpiperidin-1-yl)phenyl]piperazine수율 79.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-acetyl-4-(4-trifluoromethanesulfonyloxyphenyl)piperazine (3 g), 4-methoxy-4-phenylpiperidine (1.63 g), acetic acid palladium(II) salt (0.11 g), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.42 g) and cesium carbonate (3.88 g) in toluene (17 ml) was stirred for 30 minutes at ambient temperature. After being stirred for a further 17 hours at 100° C., the reaction mixture was diluted with dichloromethane. The suspension was filtered through celite, and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography over silica using ethyl acetate/methyl alcohol (30:1) as the elution to give 1-acetyl-4-[4-(4-methoxy-4-phenylpiperidin-1-yl)phenyl]piperazine (2.65 g).

후처리

  1. stirringAfter being stirred for a further 17 hours at 100° C.
  2. filtrationThe suspension was filtered through celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography over silica
  5. washas the elution

출처 및 근거

ORD 기록
ord-6cce7c9cc5d448bc90ed36f5d8764732
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884868B1

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