Triethylamine → 1,3-dimethyl-6-[4-(3-[3-nitrophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1729277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1729277
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][CH2:9][CH2:10]Br)([O-:3])=[O:2].[CH3:15][N:16]1[C:21]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:20][C:19](=[O:28])[N:18]([CH3:29])[C:17]1=[O:30].C(N(CC)CC)C>O1CCOCC1>[CH3:15][N:16]1[C:21]([N:22]2[CH2:27][CH2:26][N:25]([CH2:10][CH2:9][CH2:8][O:7][C:6]3[CH:12]=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH2:24][CH2:23]2)=[CH:20][C:19](=[O:28])[N:18]([CH3:29])[C:17]1=[O:30]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 71723011-(3-Bromopropoxy)-3-nitrobenzeneHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×

Produkt 1

HCID 100012161,3-dimethyl-6-[4-(3-[3-nitrophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1.69 g of the above oily compound d, 1.12 g of 1,3-dimethyl-6-(1-piperazinyl)-2,4(1H,3H)-pyrimidinedione (compound b) and 1 ml of triethylamine were heated under reflux in 20 ml of dioxane for 4 hours to carry out reaction. After completion of the reaction, insolubles were removed from the reaction mixture by filtration, and the filtrate was then concentrated. Next, the resultant residue (concentrate) was dissolved in chloroform, and the resultant chloroform solution was washed with water. Afterward, the washed organic layer was dried over anhydrous magnesium sulfate and then treated with under reduced pressure to distill off the solvent. The residue was further purified through a silica gel column chromatography (chloroform/methanol=100/1 to 25/1 in volume ratio) and then recrystallized from ethanol. The resultant crystals were collected by filtration, washed, and then dried, thereby obtaining 1.35 g of 1,3-dimethyl-6-[4-(3-[3-nitrophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound c).

Aufarbeitung

  1. customreaction
  2. customAfter completion of the reaction, insolubles
  3. customwere removed from the reaction mixture by filtration
  4. concentrationthe filtrate was then concentrated
  5. dissolutionNext, the resultant residue (concentrate) was dissolved in chloroform
  6. washthe resultant chloroform solution was washed with water
  7. dry with materialAfterward, the washed organic layer was dried over anhydrous magnesium sulfate
  8. additiontreated with under reduced pressure
  9. distillationto distill off the solvent
  10. customThe residue was further purified through a silica gel column chromatography (chloroform/methanol=100/1 to 25/1 in volume ratio)
  11. customrecrystallized from ethanol
  12. filtrationThe resultant crystals were collected by filtration
  13. washwashed
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-75d8c08de84d42d1bee0de794de58093
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05332739

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