Potassium Carbonate → 1-(4-Hydroxyphenyl)-4-[4-(4-tolyl)phthalazin-1-yl]piperazine

HRID 621509

Reaktionsgleichung

Reaktionsgleichung von HRID 621509
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[N:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)=[N:19][N:18]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2723591p-(1-Piperazinyl)phenol dihydrobromideHCID 64087591-Chloro-4-(4-methylphenyl)phthalazine

Produkt 1

HCID 140741171-(4-Hydroxyphenyl)-4-[4-(4-tolyl)phthalazin-1-yl]piperazineAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

35 mmol of 1-(4-hydroxyphenyl)piperazine dihydrobromide, 35 mmol of 1-chloro-4-(4-tolyl)phthalazine and 52.5 mmol of K2CO3 in 110 ml of absolute N,N-dimethylformamide (DMF) were reacted by the same procedure as described in Example 18. The subsequent stirring time was 2 hours at 90° C. and 7 hours at 105° C. The DMF was then removed by distillation in vacuo. The residue remaining was taken up in CH2Cl2 /water. After thorough mixing, the phases were separated, the aqueous solution was extracted a further three time with CH2Cl2, and the CH2Cl2 extracts were combined and, after drying using MgSO4, were evaporated in vacuo. The residue was mixed with 70 ml of CH2Cl2, and the substance produced in crystalline form during this procedure was filtered off under suction. This solid (1.7 g) was 1,2-dihydro-4-(4-tolyl)phthalazin-1-one, a byproduct. The filtrate was concentrated to a volume of 40-50 ml, whereupon further substance crystallized out, which was filtered off under suction. This component (4.65 g) was boiled briefly with 15 ml of methanol, and, after cooling (<10° C.), filtered off under suction and dried. At this point, 2.72 g of pure 1-(4-hydroxyphenyl)-4-[4-(4-tolyl)phthalazin-1-yl]piperazine, melting point 265°-66° C., were obtained,

Aufarbeitung

  1. customThe DMF was then removed by distillation in vacuo
  2. customAfter thorough mixing, the phases were separated
  3. extractionthe aqueous solution was extracted a further three time with CH2Cl2
  4. customafter drying
  5. customwere evaporated in vacuo
  6. additionThe residue was mixed with 70 ml of CH2Cl2
  7. customthe substance produced in crystalline form during this procedure
  8. filtrationwas filtered off under suction
  9. concentrationThe filtrate was concentrated to a volume of 40-50 ml, whereupon further substance
  10. customcrystallized out
  11. filtrationwhich was filtered off under suction
  12. temperatureafter cooling (<10° C.)
  13. filtrationfiltered off under suction
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-44f0814409104b46adf7d7a55eac56c8
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824846

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