Triethylamine → 1-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-one

HRID 1617391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617391
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[F:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[N:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[F:8][C:9]1[C:17]([C:18]([F:21])([F:19])[F:20])=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([N:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1)=[O:12]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 337214-PiperidoneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 265964893-Fluoro-2-(trifluoromethyl)isonicotinic acid

Produkt 1

HCID 584313981-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-oneAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of piperidin-4-one (1 g, 10 mmol) and 3-fluoro-2-(trifluoromethyl)isonicotinic acid (2.32 g, 11.1 mmol) in DMF (20 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (5.62 g, 12.7 mmol) and triethylamine (4.43 mL, 31.8 mmol). The mixture was stirred at room temperature overnight and diluted with EtOAc. The solution was washed with brine, dried with sodium sulfate, filtered and concentrated. Purification on silica gel with 50-100% EtOAc/hexanes gave 2.1 g (70% yield) of the title compound. LC/MS found: 291.2 (M+1)+.

Aufarbeitung

  1. washThe solution was washed with brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on silica gel with 50-100% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-241777ae01e844a589dd21892e000513
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765734B2

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