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

HRID 1634549Notes

Reaction equation

HRID 1634549 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 vacuoo 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 vacuoo
  6. custompurify by preparative TLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a4f80d44680a4c7881b8550945cfe436
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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