Iodoethane → HCID 19031067, compound

HRID 483544Notes

Reaction equation

HRID 483544 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:24]3[C:19](=[C:20]([OH:25])[CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][C:15]2=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](I)[CH3:33]>CC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:24]3[C:19](=[C:20]([O:25][CH2:32][CH3:33])[CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][C:15]2=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 19030728HCID 19030728, compound

Product 1

HCID 19031067HCID 19031067, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(1-Benzyl-4-piperidinyl)-5-hydroxy-3,4-dihydrocarbostyril (500 mg) is dissolved in acetone (20 ml) and thereto are added potassium carbonate (246 mg) and ethyl iodide (0.18 ml). The mixture is refluxed with stirring for 6.5 hours. After the reaction, the insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure. Dichloromethane is added to the resulting residue and the mixture is washed with 5% aqueous sodium hydroxide solution and then dried with magnesium sulfate. The solvent is evaporated and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1) to give 1-(1-benzyl-4-piperidinyl)-5-ethoxy-3,4-dihydrocarbostyril (0.27 g).

Workup

  1. temperatureThe mixture is refluxed
  2. customAfter the reaction
  3. customthe insoluble materials are removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. additionDichloromethane is added to the resulting residue
  6. washthe mixture is washed with 5% aqueous sodium hydroxide solution
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent is evaporated
  9. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-4e19895bcd6c4712957b3d2489452d81
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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