Reaction #2300773

Reaction equation

Water

sodium hydride

N-(4-isopropylphenyl)acetamide

butyl bromide

→

butyl(4-isopropylphenyl)amine

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   Extractionthe mixture was extracted with ethyl acetate
3. 3
   WashThe organic layer was washed
4. 4
   Otherdried
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   workup.ADDITION4N Hydrochloric acid (13 mL) was added to the residue
7. 7
   Temperaturethe mixture was refluxed for 7 hr
8. 8
   workup.ADDITIONWater was added to the reaction mixture
9. 9
   Extractionthe mixture was extracted with ethyl acetate
10. 10
    WashThe organic layer was washed
11. 11
    Otherdried
12. 12
    Concentrationconcentrated under reduced pressure

Procedure

To a solution of N-(4-isopropylphenyl)acetamide (1.8 g) in dimethylformamide (18 mL) was added, under ice-cooling, 60% sodium hydride (0.44 g). Further, butyl bromide (1.4 mL) was added and the mixture was stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure. 4N Hydrochloric acid (13 mL) was added to the residue and the mixture was refluxed for 7 hr. Water was added to the reaction mixture followed by neutralization and the mixture was extracted with ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure to give butyl(4-isopropylphenyl)amine (1.8 g).

Source