Diphenyl diselenide → Phenyl-2-aminoethyl selenide

A preferred compound is phenyl-2-aminoethyl selenide and salts thereof. Phenyl-2-aminoethyl selenide (PAESe) was synthesized by employing the following procedure. Diphenyl diselenide, 24.707 g (79.16 mmol) was dissolved into 100 ml of tetrahydrofuran THF) with steam heating. To the intensely dark red THF solution was added 9.84 ml (95 mmol, 1.2 eq.) of 50% hypophosphorous acid and the reaction was refluxed under argon for 6 hours, cooled, and diluted with 200 ml of Et2O and washed with 200 ml of 0.127 M NaOAc buffer pH 5.0 to remove the phosphoric acid by-product. Both the Et2O and the buffer were deoxygenated by bubbling argon through fritted glass for over 1 hour in order to prevent reoxidation of phenylselenol to diphenyl diselenide. The washed organic phase was then concentrated to yield a yellow oil (diselenide contaminant) with residual salt-containing water pockets The crude product was pumped down to remove residual solvent prior to distillation which yielded the desired phenylselenol (12.6g, 51% yield). pNMR (CDCl3) (s,1H) 1.54 d (m,5H) 7.35 d. Yields as high as 70% have been obtained for this reaction.

1. temperatureheating
2. temperaturethe reaction was refluxed under argon for 6 hours
3. temperaturecooled
4. washwashed with 200 ml of 0.127 M NaOAc buffer pH 5.0
5. customto remove the phosphoric acid by-product
6. customBoth the Et2O and the buffer were deoxygenated
7. customby bubbling argon through fritted glass for over 1 hour in order
8. concentrationThe washed organic phase was then concentrated

ORD record

ord-d6a9c98b13fd4bdeb7229bac6b437543

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04906668