Réaction #215510

Équation de réaction

4-Aminobenzonitrile

1-iodomethyl-2-methylcyclopentane

water

→

4-(2-methylcyclopentylmethylamino)benzonitrile

Solvants

hexamethylphosphoramide

Conditions de réaction

Traitement

1. 1
   Températureheated under nitrogen in an oil bath
2. 2
   TempératureThe reaction mixture is cooled to room temperature
3. 3
   TempératureThe mixture is then chilled in an ice bath
4. 4
   AutreThe precipitate separated
5. 5
   Filtrationis filtered
6. 6
   Lavagewashed thoroughly with water
7. 7
   Autredried
8. 8
   LavageIt is then washed repeatedly with hexane
9. 9
   Autredried
10. 10
    AutreRecrystallization from ether-hexane

Mode opératoire

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