Acetic Acid → 4-Chlorobenzylamine hydrochloride

HRID 2372334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2372334
[BH4-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=O)=[CH:6][CH:5]=1.C(O)(=O)C>O1CCOCC1>[ClH:3].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][NH2:10])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 120844-ChlorobenzamideHCID 4311764Sodium borohydride

Produkt 1

HCID 4584434-Chlorobenzylamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

Into a mixture comprising 7.30 g of sodium borohydride, 6.00 g of 4-chlorobenzamide and 100 ml of 1,4-dioxane, a mixed solution of 11.58 g of acetic acid and 30 ml of 1,4-dioxane, was dropwise added under stirring and cooling with ice over a period of 30 minutes. After the dropwise addition, the reaction mixture was refluxed under stirring for two hours. After cooling, ice pieces were gradually added to decompose the excess reducing agent, and the solvent was distilled off under reduced pressure Then, the residue was extracted with chloroform. The extract was washed with a saturated sodium chloride aqueous solution, and dried over sodium sulfate, and then the solvent was distilled off to a concentration of about 80 ml. The concentrated solution was cooled with ice, and 10 ml of a dioxane solution of 6N HCl was dropwise added thereto The precipitated solid substance was treated with methanol-ether to obtain 3.16 g of the above identified compound as a colorless powder The NMR spectrum of the free amine is as follows:

Aufarbeitung

  1. temperaturecooling with ice over a period of 30 minutes
  2. additionAfter the dropwise addition
  3. temperaturethe reaction mixture was refluxed
  4. stirringunder stirring for two hours
  5. temperatureAfter cooling
  6. additionice pieces were gradually added
  7. distillationthe solvent was distilled off under reduced pressure
  8. extractionthe residue was extracted with chloroform
  9. washThe extract was washed with a saturated sodium chloride aqueous solution
  10. dry with materialdried over sodium sulfate
  11. distillationthe solvent was distilled off to a concentration of about 80 ml
  12. temperatureThe concentrated solution was cooled with ice, and 10 ml of a dioxane solution of 6N HCl
  13. additionwas dropwise added
  14. additionThe precipitated solid substance was treated with methanol-ether
  15. customto obtain 3.16 g of the

Quellen und Nachweise

ORD-Eintrag
ord-aa120569ae7b44f3b792ce261e542e15
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05098900

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