Imidazole → HCID 44538859, compound

HRID 1619465Notes

Reaction equation

HRID 1619465 reaction equation
O[C:2]1([O:9][CH2:10][CH3:11])[CH:7]=[CH:6][C:5](O)=[CH:4][CH2:3]1.BrCC[CH2:15][CH2:16]Cl.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[NH:46]1[CH:50]=[CH:49][N:48]=[CH:47]1.[C:51]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:52]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CC(C)=O>[N:46]1([CH2:51][CH2:52][C:5]2[CH:6]=[CH:7][C:2]([O:9][CH2:10][CH2:11][CH2:15][CH2:16][N:35]3[CH2:36][CH2:37][N:32]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[O:25][CH3:24])[CH2:33][CH2:34]3)=[CH:3][CH:4]=2)[CH:50]=[CH:49][N:48]=[CH:47]1

Participants

11

Reactant 9

HCID 795ImidazoleHCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 813641-Bromo-4-chlorobutaneHCID 66909953HCID 66909953, compound

Product 1

HCID 44538859HCID 44538859, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxyphenetylalcohol (5 mmol), 1-bromo-4-chlorobutane (5 mmol), and potassium carbonate (15 mmol) was refluxed in 100 ml of acetone for 6 h. This solution was then concentrated in a rotary evaporator and diluted with ethyl acetate. This mixture was then washed with brine, and the resulting organic layer was dried and purified by column chromatography. The product was dissolved in isopropanol (50 ml) and was added with 1-(2-methoxyphenyl)-piperazine (5 mmol), sodium carbonate (15 mmol), and potassium iodide (5 mmol) at 25° C. and the reaction mixture was refluxed for 12 h. This solution was then concentrated in a rotary evaporator and diluted with methylene chloride. This mixture was then washed with brine, and the resulting organic layer was dried and purified by column chromatography. The product was dissolved in THF and was added with imidazole (15 mmol), triphenylphosphine (15 mmol), and diisopropyl azodicarboxylate (15 mmol) dropwise at 0° C. and warmed to room temperature. After 2 h, the solvent was removed and the residue was washed with brine, and then purified by column chromatography.

Workup

  1. concentrationThis solution was then concentrated in a rotary evaporator
  2. additiondiluted with ethyl acetate
  3. washThis mixture was then washed with brine
  4. customthe resulting organic layer was dried
  5. custompurified by column chromatography
  6. dissolutionThe product was dissolved in isopropanol (50 ml)
  7. temperaturethe reaction mixture was refluxed for 12 h
  8. concentrationThis solution was then concentrated in a rotary evaporator
  9. additiondiluted with methylene chloride
  10. washThis mixture was then washed with brine
  11. customthe resulting organic layer was dried
  12. custompurified by column chromatography
  13. dissolutionThe product was dissolved in THF
  14. customthe solvent was removed
  15. washthe residue was washed with brine
  16. custompurified by column chromatography

Sources & evidence

ORD record
ord-03510c61b2c4457284ea3ec6ca07054e
Source dataset
uspto-grants-2014_07
Patent number
US08772299B2

Reaction notes

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