Ethanol → N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamine

HRID 1283972

Reaktionsgleichung

Reaktionsgleichung von HRID 1283972
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12](=[O:15])[CH2:13]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([NH:30][C:31]1[CH:47]=[CH:46][C:34]([O:35][CH2:36][CH2:37][NH:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:33][CH:32]=1)(=[O:29])[CH3:28].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C(O)(C)C>[CH2:39]([N:38]([CH2:37][CH2:36][O:35][C:34]1[CH:33]=[CH:32][C:31]([NH:30][C:27](=[O:29])[CH3:28])=[CH:47][CH:46]=1)[CH2:13][C:12](=[O:15])[C:11]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 126818023,4-Dibenzyloxyphenacyl bromideHCID 22750197N-[2-(4-acetamidophenoxy)ethyl]benzylamine

Produkt 1

HCID 22750181N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamineAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 3,4-dibenzyloxyphenacyl bromide (32.8 g.), N-[2-(4-acetamidophenoxy)ethyl]benzylamine (22.8 g.), anhydrous sodium carbonate (8.4 g.) and ethanol (1 liter) was boiled under reflux for 2 hours, then filtered hot to remove the inorganic sediment and evaporated in vacuo to afford a thick syrup. The latter was dissolved in hot isopropanol and the solution cooled, the precipitated solid then being collected by filtration. To a hot solution of the solid in fresh isopropanol were added a few milliliters of ethyl acetate, and the solution was then allowed to cool to room temperature. The crystallized solid was collected by filtration, washed in diethyl ether and dried. Recrystallization from an isopropanol/ethyl acetate mixture afforded N-benzyl-N-(3,4-dibenzyloxybenzoyl)methyl-2-(4-acetamidophenoxy)ethylamine (32.8 g.), m.p. 104°-6°C.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. filtrationfiltered hot
  3. customto remove the inorganic sediment
  4. customevaporated in vacuo
  5. customto afford a thick syrup
  6. temperaturethe solution cooled
  7. filtrationthe precipitated solid then being collected by filtration
  8. additionTo a hot solution of the solid in fresh isopropanol were added a few milliliters of ethyl acetate
  9. filtrationThe crystallized solid was collected by filtration
  10. washwashed in diethyl ether
  11. customdried
  12. customRecrystallization from an isopropanol/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-740ae0bab8e74bfba8f48ec6ad15daaa
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03976783

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