1-Phenethylamine, (-)- → (S)-N-cinnamyl-alpha-methylbenzylamine

Participants

Reaction Steps

To a solution of (S)-α-methylbenzylamine (1) (0.500 g, 4.13 mmol) in toluene (20 ml) were added N-ethyldiisopropylamine (0.719 ml, 4.13 mmol) and cinnamyl chloride (0.575 ml, 4.13 mmol). The mixture was refluxed overnight, after which the toluene was removed under reduced pressure. The residue was partitioned between ethyl acetate (50 ml) and saturated sodium bicarbonate solution (30 ml) and the organic layer was washed with brine (30 ml), dried (magnesium suphate) and removed under reduced pressure to afford a yellow oil. This was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:4) to give the title compound (4) as a colourless oil (0.456 g, 47%). δH (200 MHz; CDCl3) 7.41-7.20 (10H, m, Ph), 6.50 (1H, d, J=15.9, PhCH=CH), 6.30 (1H, dt, J=15.9 and 6.1, PhCH=CH), 3.88 (1H, q, J=6.6, PhCHCH3), 3.29 (2H, d, J=6.5, NCH2), 1.56 (1H, br s, NH), 1.42 (3H, d, J=6.8, PhCHCH3).

Provenance & Evidence