Triethylamine → 1-(1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl)ethanone

HRID 454940

Reaktionsgleichung

Reaktionsgleichung von HRID 454940
C(N(CC)CC)C.[Cl:8][C:9]1[N:10]=[N:11][C:12]([Cl:16])=[CH:13][C:14]=1Cl.[NH:17]1[CH2:22][CH2:21][CH:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]1>CN(C=O)C.O>[Cl:8][C:9]1[N:10]=[N:11][C:12]([Cl:16])=[CH:13][C:14]=1[N:17]1[CH2:22][CH2:21][CH:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 951233,4,6-TrichloropyridazineHCID 27237641-(Piperidin-4-yl)ethan-1-one

Produkt 1

HCID 585479571-(1-(3,6-Dichloropyridazin-4-yl)piperidin-4-yl)ethanoneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Triethylamine (2.2 g, 20.0 mmol), 3,4,6-trichloro-pyridazine (1.8 g, 10.0 mmol) and 1-(piperidin-4-yl)ethanone (1.3 g, 10.0 mmol) was dissolved in DMF (20 mL) and the resulting mixture was stirred at room temperature overnight. The mixture was then diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were combined and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in hexanes) to give 1-(1-(3,6-dichloropyridazin-4-yl)piperidin-4-yl)ethanone (1.0 g, 3.8 mmol, 39% yield) as white solid. ESI-MS (M+1): 274 calc. for C11H13ClN3O 273.

Aufarbeitung

  1. extractionextracted with EtOAc (2×50 mL)
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9f93ca938d46472888460804cf7f0d07
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497265B2

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