Dimethylformamide → Ethyl 4-[2-[1-(6-fluoro-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoate

HRID 981646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 981646
F[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[NH:3]1.C(O)(=O)CCC(O)=O.[NH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][O:25][C:26]2[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[F:8][C:4]1[N:3]=[N:2][C:7]([N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][O:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][CH:36]=3)[CH2:21][CH2:22]2)=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 197482732,6-DifluoropyridazineHCID 23056112Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioate

Produkt 1

HCID 14989295Ethyl 4-[2-[1-(6-fluoro-3-pyridazinyl)-4-piperidinyl]ethoxy]benzoateAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture 1.2 parts of 2,6-difluoropyridazine, 4 parts of ethyl 4-[2-(4-piperidinyl)-ethoxy]benzoate butanedioate(1:1), 5.3 parts of sodium carbonate and 141 parts of N,N-dimethylformamide was stirred for 48 hours at 60° C. After cooling, the reaction mixture was poured into water. The precipitated product was filtered off, washed with water and dissolved in trichloromethane. The organic layer was dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2.4 parts (64.3%) of ethyl 4-[2-[1-(6-fluoro-3-pyridazinyl)-4-piperidinyl]-ethoxy]benzoate; mp. 131.9° C. (comp. 73).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water
  4. dissolutiondissolved in trichloromethane
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from 2-propanol
  9. filtrationThe product was filtered off
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-aba27ace058f47e68d84de4154a6232f
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04992433

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