Water → N-[5-Bromo-2-methoxy-3-(1-methoxy-1-methylethyl)phenyl]-N,N-dimethylamine

HRID 1296027Notes

Reaction equation

HRID 1296027 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:14]([CH3:16])[CH3:15])[C:5]([O:12][CH3:13])=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:7]=1.[C:17](=O)([O-])O.[Na+].O>CO.Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([O:11][CH3:17])([CH3:9])[CH3:10])[C:5]([O:12][CH3:13])=[C:4]([N:14]([CH3:16])[CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 589100492-[5-Bromo-3-(dimethylamino)-2-methoxyphenyl]-2-propanol

Product 1

HCID 22930179N-[5-Bromo-2-methoxy-3-(1-methoxy-1-methylethyl)phenyl]-N,N-dimethylamine

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

After dissolving 2-[5-bromo-3-(dimethylamino)-2-methoxyphenyl]-2-propanol (410 mg) in 100 mL of methanol-hydrochloric acid, the solution was heated to reflux for 14 hours. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogencarbonate was added for neutralization, water was added and extraction was performed with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (370 mg) as an oil. 1H-NMR (CDCl3) δ: 1.57(3H, s), 1.60(3H, s), 2.77(6H, s), 3.40(3H, s), 3.77(3H, s), 6.95(1H, d, J=2 Hz), 7.16(1H, d, J=2 Hz).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 14 hours
  3. additionwas added
  4. extractionextraction
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter distilling off the solvent under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b82abbf2bbfb4b9c9404de2d2253e9e2
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…