Sodium Hydroxide → (4-Nitrobenzyl)dipropylamine

HRID 348598

Reaktionsgleichung

Reaktionsgleichung von HRID 348598
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[OH-].[Na+]>C(Cl)(Cl)Cl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:7][CH2:8][CH3:9])[CH2:6][CH2:5][CH3:12])=[CH:11][CH:12]=1)([O-:4])=[O:3]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 112524674-Nitrobenzylamine hydrochloride

Produkt 1

HCID 15871689(4-Nitrobenzyl)dipropylamineAusbeute 146,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Commercially available 4-nitrobenzylamine hydrochloride (manufactured by Tokyo Kasei Kogyo., Ltd.) (1.82 g) was suspended in chloroform (15 ml). Then, a 1 mol/l sodium hydroxide aqueous solution (15 ml) was added to the suspension and the aqueous layer was then extracted with chloroform. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off, followed by dissolving the residue in anhydrous methanol (20 ml). Subsequently, the solution was added with propionaldehyde (1.66 ml) and sodium cyanoborohydride (1.81 g) and then adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 21 hours. After completion of the reaction, the solvent was distilled off. The residue was added with 1 mol/l sodium hydroxide and then subjected to chloroform extraction. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.67 g) as a yellow oily substance.

Aufarbeitung

  1. extractionthe aqueous layer was then extracted with chloroform
  2. dry with materialThe extract was dried with anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. dissolutionby dissolving the residue in anhydrous methanol (20 ml)
  5. additionSubsequently, the solution was added with propionaldehyde (1.66 ml) and sodium cyanoborohydride (1.81 g)
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off
  8. additionThe residue was added with 1 mol/l sodium hydroxide
  9. extractionsubjected to chloroform extraction
  10. dry with materialThe extract was dried with anhydrous magnesium sulfate
  11. distillationthe solvent was then distilled off
  12. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f296b0df65594fbfab96bd3485f2094c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176227B2

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