Potassium Carbonate → HCID 69010052, compound

HRID 217668Notes

Reaction equation

HRID 217668 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=3)[CH2:26][CH2:25]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 132191211-[(5-Bromopentyl)oxy]-3-nitrobenzene

Product 1

HCID 69010052HCID 69010052, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-(5-bromo-pentyloxy)-3-nitro-benzene (432 mg, 1.5 mmol) and 1-(4-fluoro-phenyl)-piperazine (297 mg, 1.65 mmol) in acetonitrile (5 mL) was added potassium carbonate (414 mg, 3.0 mmol). After refluxed for 6 hours, the reaction mixture was quenched with water (10 mL) followed by extraction with ethyl acetate (10 mL×3). The combined organic layers were washed with brine and then concentrated under vacuum. The resulting residue was purified by silica gel column chromatography to give 1-(4-fluoro-phenyl)-4-[5-(3-nitro-phenoxy)-pentyl]-piperazine (549 mg, 1.42 mmol, 94%) as a yellow solid.

Workup

  1. temperatureAfter refluxed for 6 hours
  2. customthe reaction mixture was quenched with water (10 mL)
  3. extractionfollowed by extraction with ethyl acetate (10 mL×3)
  4. washThe combined organic layers were washed with brine
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-21029711292b4275b18779de3c1d4377
Source dataset
uspto-grants-2012_06
Patent number
US08198284B2

Reaction notes

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