Reacción #10887

Ecuación de reacción

1-(4-nitrophenyl)piperazine

potassium carbonate

iodocyclopentane

18-crown-6

→

1-cyclopentyl-4-(4-nitrophenyl)piperazine

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux overnight
2. 2
   FiltraciónThe mixture was filtered
3. 3
   Lavadothe filter cake was washed with acetonitrile
4. 4
   OtroThe solvent was evaporated from the combined filtrates
5. 5
   Otrothe residue was partitioned between water and ethyl acetate
6. 6
   OtroThe layers were separated
7. 7
   Extracciónthe aqueous layer was extracted twice with ethyl acetate
8. 8
   SecadoThe combined organic layers were dried (Na2SO4)
9. 9
   Filtraciónfiltered
10. 10
    Otroevaporated to a yellow solid
11. 11
    Otrodried under vacuum

Procedimiento

A mixture of 1-(4-nitrophenyl)piperazine (12 g, 57.9 mmol) (Acros Organics), powdered potassium carbonate (5.4 g, 39 mmol), iodocyclopentane (7 mL, 60.8 mmol) (Aldrich) and a catalytic amount of 18-crown-6 in acetonitrile (90 mL) was heated at reflux overnight. The mixture was filtered, and the filter cake was washed with acetonitrile. The solvent was evaporated from the combined filtrates and the residue was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, evaporated to a yellow solid and dried under vacuum to give 1-cyclopentyl-4-(4-nitrophenyl)piperazine) (6.6 g, 41%.)

Fuente