Triethylamine → 4,5-dihydro-4-(1-pentafluoropropionylpiperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-one

HRID 619503

Reaktionsgleichung

Reaktionsgleichung von HRID 619503
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][N:10]2[CH2:20][C:19]3[N:21]4[C:12](=[CH:13][N:14]=[C:15]4[CH:16]=[CH:17][CH:18]=3)[C:11]2=[O:22])[CH2:5][CH2:4]1.C(N(CC)CC)C.FC(F)(F)C(F)(F)C([O:35][C:36](=O)[C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39])=O>C(#N)C>[F:42][C:37]([F:43])([C:38]([F:41])([F:40])[F:39])[C:36]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][N:10]2[CH2:20][C:19]3[N:21]4[C:12](=[CH:13][N:14]=[C:15]4[CH:16]=[CH:17][CH:18]=3)[C:11]2=[O:22])[CH2:5][CH2:4]1)=[O:35]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 67742Pentafluoropropionic anhydrideHCID 211902714,5-dihydro-4-(piperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-one dihydrochloride

Produkt 1

HCID 211901874,5-dihydro-4-(1-pentafluoropropionylpiperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-oneAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In 10 ml of acetonitrile was suspended 687 mg (2.0 mM) of 4,5-dihydro-4-(piperidin-4-ylmethyl)-3H-1,4,8b-triazaacenaphthylen-3-one dihydrochloride, followed by addition of 2.23 ml (16.0 mM) of triethylamine and 1.97 ml (10.0 mM) of pentafluoropropionic anhydride in the order mentioned. This mixture was stirred at room temperature for 1 hour and the solvent was then distilled off under reduced pressure. The residue was extracted with 50 ml of chloroform and the organic layer was washed with 50 ml of saturated aqueous NaCl solution and dried over MgSO4. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=10:1) to provide 526 mg (yield 63.2%) of the title compound as light-yellow amorphous substance.

Aufarbeitung

  1. distillationthe solvent was then distilled off under reduced pressure
  2. extractionThe residue was extracted with 50 ml of chloroform
  3. washthe organic layer was washed with 50 ml of saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-0252bce3457644bbbb16f94f784aa001
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958942

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