Potassium hydride → N-(2-butenyl)-N-[(4-chlorophenyl)methyl]-(3-pyridyl)amine

HRID 1583653

Reaktionsgleichung

Reaktionsgleichung von HRID 1583653
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.[H-].[K+].Br[CH2:19][CH:20]=[CH:21][CH3:22]>O1CCCC1>[CH2:19]([N:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:20]=[CH:21][CH3:22]

Komponenten

5

Edukt 3

HCID 82127Potassium hydrideHCID 1224142-Butene, 1-bromo-HCID 10036347N-(4-Chlorobenzyl)pyridin-3-amine

Produkt 1

HCID 54513041N-(2-butenyl)-N-[(4-chlorophenyl)methyl]-(3-pyridyl)amineAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4.4 g of N-[(4-chlorophenyl)methyl]-(3-pyridyl)amine dissolved in 50 ml of tetrahydrofuran was added to a suspension of 4 g of a 24.6% suspension of potassium hydride in oil in tetrahydrofuran. The mixture was allowed to stir at room temperature for approximately 30 minutes whereupon 4 g of 1-bromo-2-butene was added dropwise to the reaction mixture. The mixture was allowed to stir at room temperature overnight at which time the solution was evaporated to dryness. The residue was dissolved in dichloromethane and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The oil residue was chromatographed over silica gel. Fractions containing the major component were combined and the solvent was evaporated therefrom to provide 3 g of N-(2-butenyl)-N-[(4-chlorophenyl)methyl]-(3-pyridyl)amine as an oil.

Aufarbeitung

  1. additionwas added dropwise to the reaction mixture
  2. customwas evaporated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe oil residue was chromatographed over silica gel
  9. additionFractions containing the major component
  10. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c8d0fcc40cb94070ab4cc37bf1690e53
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04552960

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