Isopropyl iodide → HCID 15239440, compound

HRID 1609495Notes

Reaction equation

HRID 1609495 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:18])[N:9]2[CH3:19])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:26](I)([CH3:28])[CH3:27]>O>[CH:26]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:18])[N:9]2[CH3:19])=[CH:6][CH:7]=1)([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 15239439HCID 15239439, compound

Product 1

HCID 15239440HCID 15239440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 ml of a solution containing 1.50 g of 3-(4-hydroxyphenyl)-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline, 0.86 g of potassium carbonate and 1.24 ml of isopropyl iodide were added and the resulting mixture was heated to reflux for 21 hours. After allowing the mixture to cool, water was added thereto and the resultant was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography [hexane/ethyl acetate (2/1)] to obtain 1.53 g of 3-(4-isopropyloxyphenyl)-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. additionwere added
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 21 hours
  4. temperatureto cool
  5. extractionthe resultant was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter evaporating the solvent under reduced pressure
  9. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate (2/1)]

Sources & evidence

ORD record
ord-b2a5368e68e941f89af10e2bbcc065bc
Source dataset
uspto-grants-1995_03
Patent number
US05401752

Reaction notes

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