Reaction #1022

Reaction equation

water

2-amino-1-propanol

sodium hydride

4-bromobenzonitrile

→

desired product

Yield 41.0%

2-(4-cyanophenoxy)-1-methylethylamine

Yield 41.0%

Solvents

N,N-dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise to the reaction mixture
2. 2
   OtherAfter completion of the reaction
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic layer was washed with water
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   OtherThe ethyl acetate was removed under reduced pressure
7. 7
   workup.DISTILLATIONThe residue was distilled under reduced pressure

Procedure

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.

Source