Methyl Chloride → UM-424

HRID 1733354Notes

Reaction equation

HRID 1733354 reaction equation
[CH:1]([N:4]([CH2:6][CH:7]([OH:22])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:5])([CH3:3])[CH3:2].[CH3:23][Cl:24]>CC(C)=O>[Cl-:24].[C:16]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH:7]([OH:22])[CH2:6][N+:4]([CH:1]([CH3:3])[CH3:2])([CH3:23])[CH3:5])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6327Methyl ChlorideHCID 203012641-[([1,1'-Biphenyl]-2-yl)oxy]-3-[methyl(propan-2-yl)amino]propan-2-ol

Product 1

HCID 194064UM-424

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 10.0 g (0.033 moles) of 1-(N-isopropyl-N-methylamino)-3-(2-phenylphenoxy)propan-2ol and 30 ml of acetone, placed in a pressure container cooled in a Dry Ice-acetone bath is added 30 ml of methyl chloride. The container is sealed and mixture stirred at room temperature for about 8 days, after which time the mixture is again cooled in a Dry Ice-acetone bath. The container is opened slowly to permit reduction of any excess pressure and the solvent and excess methyl chloride is removed by evaporation under reduced pressure. The material remaining is dissolved in 30 ml of absolute ethanol, which then is evaporated under reduced pressure. The latter procedure is repeated and the residue is crystallized from anhydrous acetone to afford [3-(2-phenylphenoxy)-2-hydroxypropyl]isopropyldimethylammonium chloride melting at about 124°-127° C. and represented structurally by the following formula ##STR7##

Workup

  1. temperaturecooled in a Dry Ice-acetone bath
  2. customThe container is sealed
  3. temperatureafter which time the mixture is again cooled in a Dry Ice-acetone bath
  4. customthe solvent and excess methyl chloride is removed by evaporation under reduced pressure
  5. dissolutionThe material remaining is dissolved in 30 ml of absolute ethanol
  6. customwhich then is evaporated under reduced pressure
  7. customthe residue is crystallized from anhydrous acetone

Sources & evidence

ORD record
ord-c9061d94b40741a3aff1e48c9f0ff787
Source dataset
uspto-grants-1980_12
Patent number
US04241088

Reaction notes

Loading…