Ethanolamine → 2-((1-Phenylethyl)amino)ethan-1-ol

Participants

Reaction Steps

A mixture of acetophenone (2.00 g, 16.6 mmol, Eq: 1.00), 2-aminoethanol (3.05 g, 49.9 mmol, Eq: 3.00) and titanium(IV) isopropoxide (6.15 g, 6.41 ml, 21.6 mmol, Eq: 1.3) in absolute methanol (25 ml) was stirred under nitrogen at room temperature for 48 hrs. Sodium borohydride (630 mg, 16.6 mmol, Eq: 1.00) was then added at 0° C. and the resulting mixture was stirred for an additional 2 hr. The reaction was then quenched by adding water (1 ml). Stirring was continued at room temperature for 20 min., then the reaction mixture was acidified with 1N HCl. After filtration over a pad of Celite, washing with ethyl acetate, any drying over magnesium sulfate, the mixture was concentrated to obtain 2-(1-phenylethylamino)ethanol (oil, 2.71 g, 16.4 mmol, 98.5% yield).

Provenance & Evidence