Potassium Carbonate → 1-(4-Hydroxyphenyl)-4-(3-cyano-4-methyl-6-phenylpyrid-2-yl)piperazine

HRID 621512

Reaktionsgleichung

Reaktionsgleichung von HRID 621512
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:22]([C:23]#[N:24])=[C:21]([CH3:25])[CH:20]=[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:17]3[C:22]([C:23]#[N:24])=[C:21]([CH3:25])[CH:20]=[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:18]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 8336882-Chloro-4-methyl-6-phenylnicotinonitrileHCID 2723591p-(1-Piperazinyl)phenol dihydrobromide

Produkt 1

HCID 140741181-(4-Hydroxyphenyl)-4-(3-cyano-4-methyl-6-phenylpyrid-2-yl)piperazineAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

12.26 g (36 mmol) of 1-(4-hydroxyphenyl)piperazine dihydrobromide, 8.24 g (36.1 mmol) of 2-chloro-3-cyano-4-methyl-6-phenylpyridine and 7.46 g (54 mmol) of powdered K2CO3 in 135 ml of absolute DMF were reacted at 90° C. according to the procedure described in Example 20. The mixture was subsequently stirred for 10 hours at 110° C. After removal of the DMF by distillation, the residue was taken up in CH2Cl2 /water. After thorough mixing, separating the phases and extraction of the aqueous solution, the CH2Cl2 extracts were combined, dried and evaporated. The crystalline residue (14.6 g) was recrystallized three times as follows. The substance was dissolved in a boiling mixture of CH2Cl2 /CH3OH 1:1, and the majority of the CH2Cl2 was then removed by distillation. A product crystallized out of the CH3OH solution obtained, and was filtered off under suction and again recrystallized in this fashion. Further impure substance was isolated from the mother liquors by concentration etc, and this was finally recrystallized again as described above. In this fashion, 6.82 g (=51% yield) of 1-(4-hydroxyphenyl)-4-(3-cyano-4-methyl-6-phenylpyrid-2-yl)piperazine, melting point 207°-08° C., were obtained;

Aufarbeitung

  1. customAfter removal of the DMF
  2. distillationby distillation
  3. customAfter thorough mixing, separating
  4. extractionthe phases and extraction of the aqueous solution
  5. customdried
  6. customevaporated
  7. customThe crystalline residue (14.6 g) was recrystallized three times
  8. dissolutionThe substance was dissolved in a boiling mixture of CH2Cl2 /CH3OH 1:1
  9. customthe majority of the CH2Cl2 was then removed by distillation
  10. customA product crystallized out of the CH3OH solution
  11. customobtained
  12. filtrationwas filtered off under suction
  13. customagain recrystallized in this fashion
  14. customFurther impure substance was isolated from the mother liquors by concentration etc
  15. customthis was finally recrystallized again

Quellen und Nachweise

ORD-Eintrag
ord-03f23008a32843ecb952b831ce8d8401
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824846

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