Potassium Carbonate → N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide

HRID 591790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591790
BrC[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH:18]([N:21]([CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:22](=[O:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][N:28]2[CH2:29][CH2:30][CH:25]([N:21]([CH:18]([CH3:20])[CH3:19])[C:22](=[O:24])[CH3:23])[CH2:26][CH2:27]2)=[CH:11][CH:10]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 110851354-(2-Bromoethyl)benzaldehydeHCID 23369939N-isopropyl-N-(piperidin-4-yl)acetamide

Produkt 1

HCID 86662036N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4-(bromoethyl)benzaldehyde (0.840 g, 4.2 mmol) and K2CO3 (1.75 g, 12.6 mmol) in DMF (15 mL) was added N-isopropyl-N-(piperidin-4-yl)acetamide (0.92 g, 4.2 mmol) and the reaction was stirred at room temperature 5 hours, then concentrated in vacuo. The resulting mixture was diluted with H2O and extracted with EtOAc. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, afforded N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide (0.770 g, 61%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionThe resulting mixture was diluted with H2O
  3. extractionextracted with EtOAc
  4. washThe organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 1% to 10% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-510d241cc99b49c193ede95e9eabbcd2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238640B2

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