Reaction #215510

Reaction equation

4-Aminobenzonitrile

1-iodomethyl-2-methylcyclopentane

water

→

4-(2-methylcyclopentylmethylamino)benzonitrile

Solvents

hexamethylphosphoramide

Conditions

Workup

1. 1
   Temperatureheated under nitrogen in an oil bath
2. 2
   TemperatureThe reaction mixture is cooled to room temperature
3. 3
   TemperatureThe mixture is then chilled in an ice bath
4. 4
   OtherThe precipitate separated
5. 5
   Filtrationis filtered
6. 6
   Washwashed thoroughly with water
7. 7
   Otherdried
8. 8
   WashIt is then washed repeatedly with hexane
9. 9
   Otherdried
10. 10
    OtherRecrystallization from ether-hexane

Procedure

4-Aminobenzonitrile (11.8 g.) and 1-iodomethyl-2-methylcyclopentane (16.3 g.) are dissolved in hexamethylphosphoramide (100 ml.) and heated under nitrogen in an oil bath maintained at 120° C. for 22 hours. The reaction mixture is cooled to room temperature and water (100 ml.) is added gradually. The mixture is then chilled in an ice bath. The precipitate separated is filtered, washed thoroughly with water, and dried. It is then washed repeatedly with hexane and dried. Recrystallization from ether-hexane affords 4-(2-methylcyclopentylmethylamino)benzonitrile as pale yellow crystals.

Source