Sodium hydride → Tert-butyl 4-(pyridin-2-ylmethyl)piperazine-1-carboxylate

HRID 713713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713713
[H-].[Na+].[N:3]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:6]1[CH2:7][CH2:8][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5642092-(Bromomethyl)pyridine

Produkt 1

HCID 10062065Tert-butyl 4-(pyridin-2-ylmethyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension of 0.28 g (0.71 mmol) of sodium hydride (60% mineral oil dispersion) in 5 mL anhydrous N,N-dimethylformamide at 0° C. was added 0.12 g (0.65 mmol) tert-butyl 1-piperazine-carboxylate. The resulting mixture was stirred under an atmosphere of nitrogen for 15 min and then allowed to warm to ambient temperature at which point 0.14 g (0.59 mmol) of 2-(bromomethyl)pyridine was added. After 4 h, quench the reaction with 25 mL cold water and extract the resulting solution with 25 mL ethyl acetate. The organic layer was washed with water (2×25 mL), dried over magnesium sulfate, filtered and evaporated in vacuo to afford the title compound which was purified by reverse-phase HPLC (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). LC/MS: m/z (ES) 278.1 (MH)+.

Aufarbeitung

  1. additionwas added
  2. waitAfter 4 h
  3. customquench
  4. customthe reaction with 25 mL cold water
  5. extractionextract the resulting solution with 25 mL ethyl acetate
  6. washThe organic layer was washed with water (2×25 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1730713aafb74215b6b84f71721337e5
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09186354B2

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