Dimethylethylamine → N-(4-Ethoxy-3-methoxy-phenethyl)-ethylenediamine

HRID 1792261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792261
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1.[AlH3].N(CC)(C)C>C1COCC1>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][NH:4][CH2:3][CH2:2][NH2:1])=[CH:8][C:9]=1[O:16][CH3:17])[CH3:15]

Komponenten

5

Edukt 3

HCID 11723DimethylethylamineHCID 14488Aluminum hydrideHCID 22034123N-(2-amino-ethyl)-2-(4-ethoxy-3-methoxy-phenyl)acetamide

Produkt 1

HCID 22034119N-(4-Ethoxy-3-methoxy-phenethyl)-ethylenediamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Treat a solution of N-(2-amino-ethyl)-2-(4-ethoxy-3-methoxy-phenyl)acetamide (0.7 g, 2.77 mmol) in THF (10 mL) with AlH3.NMe2Et (55 mL, 27.74 mmol) and heat to reflux for 14 h. Cool the resulting mixture to ambient temperature, quench with Na2CO3.10H2O (0.5 g) and stir at ambient temperature for 15 min. Filter the solution through Celite and wash with several portions of CH2Cl2. Concentrate the filtrate in vacuoo and purify by preparative TLC (10% MeOH in CH2Cl2) to obtain the title compound as a white oil.

Aufarbeitung

  1. temperatureto reflux for 14 h
  2. customquench with Na2CO3.10H2O (0.5 g)
  3. filtrationFilter the solution through Celite
  4. washwash with several portions of CH2Cl2
  5. concentrationConcentrate the filtrate in vacuoo
  6. custompurify by preparative TLC (10% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-f807ff24e2804cd888c618644e5b2c6f
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074929B2

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