Potassium Carbonate → 1-(4-Methoxyphenyl)-4-(5-nitro-2-pyridinyl)piperazine

HRID 266062

Reaktionsgleichung

Reaktionsgleichung von HRID 266062
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=3)[CH2:13][CH2:12]2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochloride

Produkt 1

HCID 37426761-(4-Methoxyphenyl)-4-(5-nitro-2-pyridinyl)piperazineAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 36 g of 1-(4-methoxyphenyl)piperazine dihydrochloride, 22 g of 2-chloro-5-nitropyridine, 58 g of potassium carbonate and 227 ml of dimethyl sulfoxide was stirred overnight at 140° C. The reaction mixture was cooled and poured onto water. The precipitated product was filtered off, washed with water and dissolved in dichloromethane. The solution was treated with activated charcoal. The latter is filtered off and the filtrate was evaporated. The residue was triturated in 2-propanol. The product was filtered off and crystallized from 1-butanol, yielding 24.5 g of 1-(4-methoxyphenyl)-4-(5-nitro-2-pyridinyl)piperazine; mp. 170° C. (interm. 21).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. dissolutiondissolved in dichloromethane
  6. additionThe solution was treated with activated charcoal
  7. filtrationThe latter is filtered off
  8. customthe filtrate was evaporated
  9. customThe residue was triturated in 2-propanol
  10. filtrationThe product was filtered off
  11. customcrystallized from 1-butanol

Quellen und Nachweise

ORD-Eintrag
ord-0a116ba728584cf7b32d9a1d3add1357
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650411

Verknüpfte Notizen

Wird geladen…