Potassium Carbonate → 1-Cyclopentyl-4-(4-nitrophenyl)piperazine

HRID 2213896Notes

Reaction equation

HRID 2213896 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH:23]1([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 73784IodocyclopentaneHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 219589211-Cyclopentyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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%)

Workup

  1. temperatureat reflux overnight
  2. filtrationThe mixture was filtered
  3. washthe filter cake was washed with acetonitrile
  4. customThe solvent was evaporated from the combined filtrates
  5. customthe residue was partitioned between water and ethyl acetate
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted twice with ethyl acetate
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated to a yellow solid
  11. customdried under vacuum

Sources & evidence

ORD record
ord-ff6acf3f670948d28428166fdc85f4b7
Source dataset
uspto-grants-2006_09
Patent number
US07105670B2

Reaction notes

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