N-Methylisopropylamine → 1-[([1,1'-Biphenyl]-2-yl)oxy]-3-[methyl(propan-2-yl)amino]propan-2-ol

HRID 1733353Notes

Reaction equation

HRID 1733353 reaction equation
[O:1]1[CH2:17][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:18][NH:19][CH:20]([CH3:22])[CH3:21]>CO>[CH:20]([N:19]([CH2:17][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:18])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 78485N-MethylisopropylamineHCID 978752-{[([1,1'-Biphenyl]-2-yl)oxy]methyl}oxirane

Product 1

HCID 203012641-[([1,1'-Biphenyl]-2-yl)oxy]-3-[methyl(propan-2-yl)amino]propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22.7 g (0.1 mole) of 2,3-epoxy-1-(2-phenylphenoxy)-propane is dissolved in 30 ml of methanol. Then 15 ml (0.2 moles) of methylisopropylamine is added to the reaction mixture slowly while stirring. The mixture is refluxed over a steam bath for 48 hr after which time the solvent and excess amine are evaporated under reduced pressure. The residue remaining is dissolved in 200 ml of ether and the solution washed with water. The ether phase is extracted with 5% aqueous hydrochloric acid and the aqueous extracts washed once with ether. The aqueous phase is neutralized with ammonium hydroxide, then extracted with methylene chloride. The methylene chloride extract is dried over anhydrous potassium carbonate and the solvent evaporated under reduced pressure to afford 1-(N-isopropyl-N-methylamino)-3-(2-phenylphenoxy)-propan-2-ol, as a blue-green oil.

Workup

  1. customare evaporated under reduced pressure
  2. dissolutionThe residue remaining is dissolved in 200 ml of ether
  3. washthe solution washed with water
  4. extractionThe ether phase is extracted with 5% aqueous hydrochloric acid
  5. washthe aqueous extracts washed once with ether
  6. extractionextracted with methylene chloride
  7. extractionThe methylene chloride extract
  8. dry with materialis dried over anhydrous potassium carbonate
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-dae9eec7c8464f91bd37f7777855d631
Source dataset
uspto-grants-1980_12
Patent number
US04241088

Reaction notes

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