Dimethyl Sulfoxide → 1-Phenethylamine

Participants

Reaction Conditions

Reaction Steps

Solid, powdered potassium hydroxide (4.6 mg, 8.2×10-5 mol) and (R)-1-phenylethylamine (98% ee) (1.00 g, 8.25×10-3 mol) are mixed with dimethyl sulfoxide (5 ml, 0.07 mol), and the mixture is heated to 80°C. and kept at this temperature for 16 h. The mixture is then cooled and diluted with water (5 ml), and the amine is extracted into ether (2×10 ml). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated to give 0.85 g (85%) of substantially racemic 1-phenylethylamine; purity >96% by 1HNMR, ratio (S):(R) recovered by HPLC with chiral column as 1:1.

Provenance & Evidence