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

Participants

Reaction Steps

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.

Provenance & Evidence