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

HRID 1290490

Reaction equation

HRID 1290490 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-34b62b3defd64b40ab61bffb4a64cd9e
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Linked notes

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