Réaction #992745

Équation de réaction

(±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

Potassium tert-butoxide

morpholine

4-bromo-2,6-dimethylaniline

→

title compound

Rendement 41.0%

2,6-Dimethyl-4-morpholin-4-yl-phenylamine

Rendement 41.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was heated
2. 2
   Températureto reflux for 16 hours under argon
3. 3
   Températurecooled
4. 4
   Filtrationfiltered through silica (200 g)
5. 5
   workup.ADDITIONBrine (250 mL) was added
6. 6
   Extractionthe mixture was extracted with ethyl acetate (3×200 mL)
7. 7
   SéchageThe combined organic phases were dried over magnesium sulfate
8. 8
   Concentrationconcentrated in vacuo
9. 9
   workup.DISSOLUTIONThe crude product was dissolved in diethyl ether (250 mL)
10. 10
    Filtrationfiltered through silica (200 g)
11. 11
    Concentrationconcentrated in vacuo

Mode opératoire

Bis(dibenzylideneacetone)palladium (2.88 g) and (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.69 g) were added to dry toluene (175 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (7.06 g), morpholine (8.7 mL) and 4-bromo-2,6-dimethylaniline (10.03 g) were added subsequently. The reaction mixture was heated to reflux for 16 hours under argon, cooled and filtered through silica (200 g). Brine (250 mL) was added and the mixture was extracted with ethyl acetate (3×200 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was dissolved in diethyl ether (250 mL), filtered through silica (200 g) and concentrated in vacuo to furnish 8.5 g (41% yield) of the title compound as a dark oil. The product was used without further purification. GC-MS (m/z) 206 (M+); tR=6.90. 1H NMR (500 MHz, CDCl3): 2.18 (s, 6H), 3.02 (m, 4H), 3.85 (m, 4H), 6.62 (b, 2H).

Source