1-(4-Pyridyl)piperazine → Methyl 4-[3-[4-(4-pyridyl)piperazin-1-yl]-2-methylpropanoyl]phenoxyacetate

HRID 266754

反応式

HRID 266754 の反応式
[CH3:1][C:2](Br)([CH3:17])[C:3]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1>C(#N)C>[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([CH2:1][CH:2]([CH3:17])[C:3]([C:5]3[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:29][CH2:30]2)=[CH:21][CH:20]=1

参加物

4

反応物 2

HCID 705171-(4-Pyridyl)piperazineHCID 18918473Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate

生成物 1

HCID 18918555Methyl 4-[3-[4-(4-pyridyl)piperazin-1-yl]-2-methylpropanoyl]phenoxyacetate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A stirred mixture of methyl 4-(2,2-dimethylbromoacetyl)-phenoxyacetate (3.15 g), and 1-(4-pyridyl)piperazine (3.26 g) in acetonitrile (200 ml) was heated at reflux temperature for 4 days. The solvent was removed in vacuo and the residue partioned between dichloromethane/water. The organic phase was dried (MgSO4), evaporated and then purified by flash chromatography on silica, eluting with 2 to 5% v/v methanol/dichloromethane. Further purification by flash chromatography on neutral alumina, eluting with dichloromethane, gave the title compound, 350 mg, as a clear oil: NMR (d6DMSO) δ 8.12 (2H, d), 7.98 (2H, d), 7.04 (2H, d), 6.75 (2H, d), 4.92 (2H, s), 3.86 (1H,m), 3.71 (3H, s), 3.19 (.4H, t), 2.70 (1H, q), 2.49 (DMSO+4H), 2.36 (1H, q), 1.09 (3H, s), trace of dichloromethane; m/e 398 (H+H)+ ; calculated for C22H27N3O4.0.1 CH2Cl2 : C, 65.3; H, 6.7; N, 10.3. found: C, 65.1; H, 6.9; N, 10.1%.

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature for 4 days
  3. customThe solvent was removed in vacuo
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. custompurified by flash chromatography on silica
  7. washeluting with 2 to 5% v/v methanol/dichloromethane
  8. customFurther purification by flash chromatography on neutral alumina
  9. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-53e3028139594a4b8e5e101d140dcc71
出典データセット
uspto-grants-1997_07
特許番号
US05652242

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