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

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).

1. temperatureThe mixture was refluxed overnight
2. customafter which the toluene was removed under reduced pressure
3. customThe residue was partitioned between ethyl acetate (50 ml) and saturated sodium bicarbonate solution (30 ml)
4. washthe organic layer was washed with brine (30 ml)
5. dry with materialdried (magnesium suphate)
6. customremoved under reduced pressure
7. customto afford a yellow oil
8. customThis was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:4)

ORD record

ord-8d607ea7136142e5b872e3012b979473

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06037498