Potassium hydride → Methyl 4-[2-[4-(4-pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetate

HRID 1290490

反応式

HRID 1290490 の反応式
[H-].[K+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][C:11](=[O:15])[CH2:10]2)=[CH:5][CH:4]=1.Br[CH2:17][C:18]([C:20]1[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=1)=[O:19]>CN(C=O)C>[N:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:17][C:18]([C:20]3[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)=[O:19])[C:11](=[O:15])[CH2:10]2)=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 82127Potassium hydrideHCID 243438Methyl 4-bromoacetylphenoxyacetateHCID 189183564-(Pyridin-4-YL)piperazin-2-one

生成物 1

HCID 18918332Methyl 4-[2-[4-(4-pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A dispersion of potassium hydride in mineral oil (35% w/w, 0.63 g) was added to a stirred suspension of 4-(4-pyridyl)piperazin-2-one (0.885 g) in DMF (10 ml) and the mixture was stirr-ed at room temperature for 2 hours. To the anion thus formed, was added methyl 4-bromoacetylphenoxyacetate (1.44 g) and the mixture was stirred at room temperature for 20 hours. Solvent was evaporated and the residue partitioned between dichloromethane (20 ml) and water (20 ml). The organic layer was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography, the product being eluted with 1/9/0.1 v:v:v methanol/dichloromethane/0.88 S.G aqueous ammonia. Recrystallisation from ethyl acetate gave the title compound, m.p. 164°-165° C.; NMR (d6DMSO) δ 8.2(2H,d), 7.97(2H,d), 7.08(2H,d), 6.83(2H,d), 4.93(4H,d), 4.02(2H,s), 3.71(3H,s), 3.7(2H,m), 3.52(2H,m); m/e 384 (M+H)+ ; calculated for C20H21N3O5 : C, 62.7; H, 5.52; N, 11.0. Found: C, 62.6; H, 5.6; N, 10.9%.

後処理

  1. customTo the anion thus formed
  2. customSolvent was evaporated
  3. customthe residue partitioned between dichloromethane (20 ml) and water (20 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash column chromatography
  7. washthe product being eluted with 1/9/0.1 v
  8. customRecrystallisation from ethyl acetate

出典と根拠

ORDレコード
ord-34b62b3defd64b40ab61bffb4a64cd9e
出典データセット
uspto-grants-1998_05
特許番号
US05750754

関連ノート

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