Piperidine → HCID 86638135, Verbindung

HRID 1931442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931442
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:12])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 730125963-(6-bromopyridin-3-yl)propanoic acid

Produkt 1

HCID 86638135HCID 86638135, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

9 g (39 mmol) of 3-(6-bromo-pyridin-3-yl)-propionic acid, 22.5 g (195 mmol) of NEM and 12.83 g (39 mmol) of TOTU were dissolved in 30 ml of DMF and stirred at room temperature for 15 min. 3.33 g (39 mmol) of piperidine were, and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with a saturated sodium hydrogencarbonate solution. The organic phase was dried with sodium sulfate, filtered, and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography. Yield: 10.2 g.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 16 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with a saturated sodium hydrogencarbonate solution
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d257becf78ed4c05ac19c6aa0ee23374
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188291B2

Notizen zur Reaktion

Wird geladen…