Reaction #10887

Reaction equation

1-(4-nitrophenyl)piperazine

potassium carbonate

iodocyclopentane

18-crown-6

→

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

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureat reflux overnight
2. 2
   FiltrationThe mixture was filtered
3. 3
   Washthe filter cake was washed with acetonitrile
4. 4
   OtherThe solvent was evaporated from the combined filtrates
5. 5
   Otherthe residue was partitioned between water and ethyl acetate
6. 6
   OtherThe layers were separated
7. 7
   Extractionthe aqueous layer was extracted twice with ethyl acetate
8. 8
   DryingThe combined organic layers were dried (Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Otherevaporated to a yellow solid
11. 11
    Otherdried under vacuum

Procedure

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%.)

Source