Water → N-[4-[[2-Hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]aminomethyl]phenyl]methanesulfonamide hydrochloride

HRID 728825Notes

Reaction equation

HRID 728825 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][CH3:15])=[CH:8][CH:7]=2)[CH2:2]1.[ClH:16].[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=1.O>CON[C@H](C(O)=O)CC1N=CNC=1.[OH-].[K+].CO>[ClH:16].[OH:1][CH:3]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][CH3:15])=[CH:8][CH:7]=1)[CH2:2][NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 962WaterHCID 92515((p-(2-Methoxyethyl)phenoxy)methyl)oxiraneHCID 27609964-(Methylsulfonylamino)benzylamine hydrochloride

Product 1

HCID 67689935N-[4-[[2-Hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]aminomethyl]phenyl]methanesulfonamide hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolventHCID 178502851MeOHisSolvent

Procedure

1,2-epoxy-3-[4-(2-methoxyethyl)phenoxy]propane (63.7 mmol) in 15 mL of MeOHis added dropwise to a solution of N-[4-(aminomethyl)phenyl]methanesulfonamide hydrochloride (62.4 mmol) in 1M KOH in MeOH (65 mL) at room temperature. H2O (5 mL) is added ad the mixture is refluxed overnight. Methanol is removed from the cooled mixture under reduced pressure, and the residue is partitioned between H2O and CH2Cl2, and the combined organic portions are washed with brine and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure the hydrochloride salt is formed and recrystallized with CH3CN/MeOH to yield the title compound.

Workup

  1. temperatureis refluxed overnight
  2. customMethanol is removed from the cooled mixture under reduced pressure
  3. customthe residue is partitioned between H2O and CH2Cl2
  4. washthe combined organic portions are washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customAfter removal of the solvent under reduced pressure the hydrochloride salt
  7. customis formed
  8. customrecrystallized with CH3CN/MeOH

Sources & evidence

ORD record
ord-5c31cd1d8aa349ea9f35a71853cf0cf4
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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