Reaktion #613166

Reaktionsgleichung

N-phenylnaphthalen-1-amine

4-iodoanisole

K2CO3

18-crown-6

→

Compound 5

Ausbeute 35.0%

N-(4-methoxyphenyl)-N-phenylnaphthalen-1-amine

Ausbeute 35.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed
2. 2
   Temperaturheated
3. 3
   Temperaturto reflux for overnight under argon
4. 4
   FiltrationAfter the salt and copper were filtered off
5. 5
   workup.ADDITIONthe solution was poured into water (300 mL)
6. 6
   Extraktionextracted with DCM (2×300 mL)
7. 7
   Waschenwashed with brine
8. 8
   Trocknendried over Na2SO4
9. 9
   Sonstigepurified by flash column (5 to 20% DCM in hexanes)
10. 10
    SonstigeThe desired fraction was collected
11. 11
    Einengenconcentrated
12. 12
    Sonstigerecrystallized in ethyl acetate/methanol

Vorschrift

A mixture of N-phenylnaphthalen-1-amine (5.0 g, 22.8 mmol), 4-iodoanisole (8.0 g, 34.2 mmol), copper powder (2.89 g, 45.6 mmol), K2CO3 (12.59 g, 91.2 mmol) and 18-crown-6 (0.607 g, 2.3 mmol) in DMF (200 mL) was degassed and heated to reflux for overnight under argon. After the salt and copper were filtered off, the solution was poured into water (300 mL), and extracted with DCM (2×300 mL). The organic phase was combined and washed with brine, dried over Na2SO4, loaded on silica gel, purified by flash column (5 to 20% DCM in hexanes). The desired fraction was collected, concentrated, and recrystallized in ethyl acetate/methanol to obtain a white solid (Compound 5) (2.59 g, in 35% yield).

Quelle