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

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.

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)

ORD record

ord-dbd69dd72fcb4c82843bdc376b7a22c5

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2