Benzene → N-(2-vinyloxyethyl)-alpha-methyl-beta-phenylethylamine

HRID 1973917

Reaktionsgleichung

Reaktionsgleichung von HRID 1973917
[C:1]1([CH2:7][C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]([O:13][CH2:14][CH2:15][NH2:16])=[CH2:12].C1C=CC=CC=1.[BH4-].[Na+]>O>[CH:11]([O:13][CH2:14][CH2:15][NH:16][CH:8]([CH3:9])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:12]

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 7678PhenylacetoneHCID 4311764Sodium borohydrideHCID 52228442-(Ethenyloxy)ethan-1-amine

Produkt 1

HCID 21491005N-(2-vinyloxyethyl)-alpha-methyl-beta-phenylethylamineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 40.2 g. (0.3 mole) of phenylacetone, 26.2 g. (0.3 mole) of 2-aminoethyl vinyl ether and 200 cc. of anhydrous benzene were heated under reflux under a DeanStart water separator until the theoretical amount of water was removed (ca. 4 hours). At the end of this time, the benzene was removed under vacuum and the resulting crude imine was taken up in 450 cc. of dry methanol. To this solution was added 22.6 g. (0.6 mole) of sodium borohydride in small portions over a period of 1/2 hour. After the addition was complete, the reaction mixture was refluxed for 3 hours. The methanol was removed under vacuum and 300 cc. of water, 150 cc. of 20% potassium hydroxide and 60 g. of potassium hydroxide were added successively and the resulting oil was extracted with ether. After drying the ether solution over anhydrous magnesium sulfate, filtering and concentrating the resulting oil, it was distilled. 32.5 g. (64% yield) of the product as a colorless oil was obtained, b.p. 100°-102°/1.5 mm; ND25 1.5070.

Aufarbeitung

  1. customwas removed (ca. 4 hours)
  2. customAt the end of this time, the benzene was removed under vacuum
  3. additionTo this solution was added 22.6 g
  4. additionAfter the addition
  5. temperaturethe reaction mixture was refluxed for 3 hours
  6. customThe methanol was removed under vacuum and 300 cc
  7. additionof potassium hydroxide were added successively
  8. extractionthe resulting oil was extracted with ether
  9. dry with materialAfter drying the ether solution over anhydrous magnesium sulfate
  10. filtrationfiltering
  11. concentrationconcentrating the resulting oil, it
  12. distillationwas distilled

Quellen und Nachweise

ORD-Eintrag
ord-72fdcc0d18694c8b9c968ba7f464edaa
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03998971

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