Potassium Carbonate → Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

HRID 1848474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848474
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]#[N:29]>CC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:27][C:28]#[N:29])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate

Produkt 1

HCID 86709485Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a flask charged with ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (1.0 g, 3.8 mmol) and a stir bar was added K2CO3 (1.06 g, 7.6 mmol), bromoacetonitrile (0.92 g, 7.6 mmo0, and acetone (15 mL). The reaction was allowed to stir at RT for 2 hours. LC showed slow reaction. It was then heated to 45° C. for 3 hours. LC showed complete reaction at that point. The reaction was quenched with NH4Cl, extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The crude product was purified by MPLC to furnish the title compound. LCMS: m/z 301 (M+H)+.

Aufarbeitung

  1. customreaction
  2. temperatureIt was then heated to 45° C. for 3 hours
  3. customreaction at that point
  4. customThe reaction was quenched with NH4Cl
  5. extractionextracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by MPLC

Quellen und Nachweise

ORD-Eintrag
ord-1cb8f7b72b2542d2840e9882b42b44a7
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952166B2

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