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

HRID 1816740ノート

反応式

HRID 1816740 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6cce7c9cc5d448bc90ed36f5d8764732
出典データセット
uspto-grants-2005_04
特許番号
US06884868B1

反応ノート

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