Phenethyl bromide → N-phenethyl-3-methoxyphenethylamine

HRID 66126

Reaktionsgleichung

Reaktionsgleichung von HRID 66126
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[CH:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19]Br)=[CH:14][CH:13]=1.[OH-].[NH4+]>O>[CH2:19]([NH:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:18][C:15]1[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 7666Phenethyl bromideHCID 14923Ammonium HydroxideHCID 748663-Methoxyphenethylamine

Produkt 1

HCID 12477997N-phenethyl-3-methoxyphenethylamineAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

A mixture of 1.51 g of β-(3-methoxyphenyl)-ethylamine and 1.85 g of β-phenethyl bromide was heated to 70°-80° C. on a bath and then was progressively heated to 165° C. over 10 minutes. The mixture was held at 165° C. for 5 minutes and was then cooled. 50 ml of water and then 4 ml of concentrated ammonium hydroxide were added thereto and the mixture was extracted 3 times with 40 ml of methylene chloride. The combined organic extracts were washed with 100 ml of aqueous sodium chloride solution and was dried over magnesium sulfate and was filtered. The filtrate was evaporated to dryness to obtain 3.4 g of raw product which was chromatographed over silica gel. Elution was with a 9-1 chloroform-ethanol mixture and the homogenous fraction with an Rf = 0.45 was taken to obtain 1.2 g of N-phenethyl-3-methoxyphenethylamine in the form of a yellow oil.

Aufarbeitung

  1. temperaturewas heated to 70°-80° C. on a bath
  2. temperaturewas then cooled
  3. extractionthe mixture was extracted 3 times with 40 ml of methylene chloride
  4. washThe combined organic extracts were washed with 100 ml of aqueous sodium chloride solution
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationwas filtered
  7. customThe filtrate was evaporated to dryness
  8. customto obtain 3.4 g of raw product which
  9. customwas chromatographed over silica gel
  10. washElution

Quellen und Nachweise

ORD-Eintrag
ord-2e873c5bc63843039c95682a71050375
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04130658

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