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

Participants

Reaction Steps

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.

Provenance & Evidence