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

HRID 2121589Notes

Reaction equation

HRID 2121589 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 vacuo and purify by preparative TLC (10% MeOH in CH2Cl2) to obtain the title compound as a white oil.

Workup

  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 vacuo
  6. custompurify by preparative TLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f1b4a94bd23446f3b64585effab5c354
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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