Methyl iodide → Methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](methyl)amino]phenyl}propanoate

HRID 508025Notes

Reaction equation

HRID 508025 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)[CH:10]=1.IC.[C:31](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:31])[C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23157312Methyl 3-(4-{[(2',6'-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate

Product 1

HCID 23157638Methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](methyl)amino]phenyl}propanoateYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 3-(4-{[(2′,6′-dimethylbiphenyl-3-yl)methyl]amino}phenyl)propanoate (0.598 g, 1.60 mmol) and iodomethane (0.498 mL, 8.00 mmol) in acetone (10 mL) was added potassium carbonate (0.332 g, 2.40 mmol), and the mixture was heated under reflux under a nitrogen atmosphere for 6 hr. After cooling, the reaction mixture was concentrated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane) to give the title compound (0.297 g, yield 48%) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 6 hr
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionWater was added to the obtained residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dbd69dd72fcb4c82843bdc376b7a22c5
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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