Reacción #1022

Ecuación de reacción

water

2-amino-1-propanol

sodium hydride

4-bromobenzonitrile

→

desired product

Rendimiento 41.0%

2-(4-cyanophenoxy)-1-methylethylamine

Rendimiento 41.0%

Disolventes

N,N-dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise to the reaction mixture
2. 2
   OtroAfter completion of the reaction
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   OtroThe ethyl acetate was removed under reduced pressure
7. 7
   workup.DISTILLATIONThe residue was distilled under reduced pressure

Procedimiento

50.0 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 29.3 g of 60% sodium hydride and 300 mL of dimethylformamide at 0° C. After the reaction mixture was stirred for 30 minutes at 0° C. a solution containing 121.2 g of 4-bromobenzonitrile dissolved in N,N-dimethylformamide was added dropwise to the reaction mixture. The resultant mixture was stirred for 20 hours at room temperature. After completion of the reaction, the resultant mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The ethyl acetate was removed under reduced pressure. The residue was distilled under reduced pressure to obtain 48.0 g of the desired product (yield 41%). Boiling point: 132° C./0.26 mmHg.

Fuente