Iodoethane → HCID 23155878, compound

HRID 1714810Notes

Reaction equation

HRID 1714810 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:24])[CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:31](I)[CH3:32]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:31][CH3:32])[CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340Iodoethane3×HCID 11430Potassium Carbonate2×HCID 23155947HCID 23155947, compound

Product 1

HCID 23155878HCID 23155878, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 105 mg of 1-(4-tert-butoxycarbonylpiperazin-1-yl)-7-hydroxyisoquinoline in 10 ml of acetone, 93 mg of potassium carbonate and 55 mg of ethyl iodide were added and heated under reflux for 2 hours. Further adding 55 mg of ethyl iodide, the solution was heated under reflux for 2 hours, followed by addition of 48 mg of potassium carbonate and 55 mg of ethyl iodide, and an overnight's refluxing. Cooling the system off, the residue was extracted with ethyl acetate after addition of water, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate:n-hexane=1:4) to provide 102 mg (90%) of 1-(4-tert-butoxycarbonylpiperazin-1-yl)-7-ethoxyisoquinoline.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe solution was heated
  4. temperatureunder reflux for 2 hours
  5. temperaturean overnight's refluxing
  6. temperatureCooling the system off, the residue
  7. extractionwas extracted with ethyl acetate
  8. additionafter addition of water
  9. washwashed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was purified on silica gel column chromatography (ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-3a5678e707604d9e914f8e16d4eadc4e
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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