Potassium Carbonate → 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole

HRID 1078341

Reaktionsgleichung

Reaktionsgleichung von HRID 1078341
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][N:35]([CH2:37][CH2:38][CH2:39]Cl)[CH3:36])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]>CN(C)C=O>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][N:35]([CH2:37][CH2:38][CH2:39][O:16][C:13]2[CH:12]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:15][N:14]=2)[CH3:36])[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 220460885-(3,4-Dimethoxyphenyl)-pyrazolin-3-one

Produkt 1

HCID 152835203-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazoleAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

17 g of 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one were dissolved in 200 ml of dimethylformamide. 11 g of potassium carbonate were added to the solution and the reaction mixture was heated at 100° C. under a nitrogen atmosphere for 0.5 hours. A solution of 21 g of 3-[N-(2-(3,4-di-methoxyphenyl)-ethyl)-N-methylamino]-propylchloride in 150 ml of dimethylformamide was then added dropwise. After 2 hours the salts which formed were filtered out, the filtrate was evaporated to dryness, and the residue was dissolved in ethyl acetate. The solution was subsequently washed with 7% strength aqueous sodium hydroxide solution in order to remove unreacted 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one, dried with sodium sulfate and evaporated to dryness. The residue which remained was 35 g of oily crude product. This product was purified by chromatography over finely particulate silica gel under slightly elevated pressure (flash chromatography) using tert-butyl methyl ether/methanol 10:1 as eluent. 22.3 g of the title compound were obtained as an oil. IR spectrum of the base (as film): 1513 cm-1, 1260 cm-1, 1236 cm-1.

Aufarbeitung

  1. customAfter 2 hours the salts which formed
  2. filtrationwere filtered out
  3. customthe filtrate was evaporated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was subsequently washed with 7% strength aqueous sodium hydroxide solution in order
  6. customto remove unreacted 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one
  7. dry with materialdried with sodium sulfate
  8. customevaporated to dryness
  9. customThis product was purified by chromatography over finely particulate silica gel under slightly elevated pressure (flash chromatography)

Quellen und Nachweise

ORD-Eintrag
ord-3ded8bc18b784d46a0cc007887e859d9
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05547967

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