Allylamine → N-(3-phenylallyl)-allylamine

HRID 2259433

Reaktionsgleichung

Reaktionsgleichung von HRID 2259433
C(N(CC)CC)C.[CH2:8](Cl)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:18]([NH2:21])[CH:19]=[CH2:20]>O1CCCC1>[CH2:8]([NH:21][CH2:18][CH:19]=[CH2:20])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 7853AllylamineHCID 8471TriethylamineHCID 94242Benzene, (3-chloro-1-propenyl)-

Produkt 1

HCID 4717907N-(3-phenylallyl)-allylamineAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

175 ml (1.27 mol) of triethylamine were added to 173 ml (1.16 mol) of cinnamyl chloride in 1,350 ml of tetrahydrofuran, the mixture was heated to 60° C., and then 105 ml (1.40 mol) of allylamine were added dropwise. The mixture was refluxed for 6 h and then stirred at room temperature for 10 h. After concentration under water pump vacuum, the contents of the flask were partitioned between methyl t-butyl ether and water (pH=10). The aqueous phase was extracted twice more with methyl t-butyl ether and subsequently the combined organic phases were extracted with a mixture of 250 ml of concentrated hydrochloric acid and 2 l of water. The aqueous phase was then extracted with 1.2 l of methylene chloride, and the methylene chloride phase washed five times with 500 ml of 10% strength hydrochloric acid each time. The combined aqueous phases were made alkaline with concentrated sodium hydroxide solution and extracted twice with methylene chloride. Drying and concentration of the organic phase resulted in 66.5 g of crude product which was distilled at 86°-88° C. under oil pump vacuum (0.25 mbar). Yield: 64 g (32%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 6 h
  2. concentrationAfter concentration under water pump vacuum
  3. customthe contents of the flask were partitioned between methyl t-butyl ether and water (pH=10)
  4. extractionThe aqueous phase was extracted twice more with methyl t-butyl ether
  5. extractionsubsequently the combined organic phases were extracted with a mixture of 250 ml of concentrated hydrochloric acid and 2 l of water
  6. extractionThe aqueous phase was then extracted with 1.2 l of methylene chloride
  7. washthe methylene chloride phase washed five times with 500 ml of 10% strength hydrochloric acid each time
  8. extractionextracted twice with methylene chloride
  9. customDrying

Quellen und Nachweise

ORD-Eintrag
ord-415a2796422a4af4aa11d8764c00e038
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05473080

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