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Benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate → N-(2-aminoethyl)-N'-[2-(diisopropylamino)ethyl]urea

HRID 10463
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 10463
[CH:1]([N:4]([CH:24]([CH3:26])[CH3:25])[CH2:5][CH2:6][NH:7][C:8]([NH:10][CH2:11][CH2:12][NH:13]C(=O)OCC1C=CC=CC=1)=[O:9])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[NH3:4].[NH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:24]([CH3:26])[CH3:25])[CH:1]([CH3:2])[CH3:3])=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 21978301Benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate

Produkt 2

HCID 222AmmoniaHCID 21978253N-(2-aminoethyl)-N'-[2-(diisopropylamino)ethyl]ureaAusbeute 216,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate (Preparation 50) (6.25 g, 14.45 mmol) in ethanol (100 ml) was hydrogenated at room temperature over palladium (II) hydroxide (250 mg) for 4 hours at 414 KPa. The catalyst was removed by filtration through Arbocel (trade mark) and solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:concentrated aqueous ammonia (90:10:1, by volume) changing to dichloromethane:methanol:concentrated aqueous ammonia (90:10:2, by volume) to afford the title compound as a yellow oil (3.6 g).

Aufarbeitung

  1. customThe catalyst was removed by filtration through Arbocel (trade mark) and solvent
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-4a6dcdf464c440f5b2372f95897642bd
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07094769B2

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