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

HRID 1290490

반응식

HRID 1290490 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-34b62b3defd64b40ab61bffb4a64cd9e
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750754

연결된 노트

불러오는 중…