Sodium Hydroxide → N-[4-[(2-Hydroxy-3-phenoxypropyl)aminomethyl]phenyl]methanesulfonamide hydrochloride

HRID 728826Notes

Reaction equation

HRID 728826 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[OH-].[Na+].[O:17]1[CH:19]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18]1>CO.O>[ClH:1].[OH:17][CH:19]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:18][NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31217Phenyl glycidyl etherHCID 27609964-(Methylsulfonylamino)benzylamine hydrochloride

Product 1

HCID 67689882N-[4-[(2-Hydroxy-3-phenoxypropyl)aminomethyl]phenyl]methanesulfonamide hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 18.0 g (0.76 mmol) of N-[4-(aminomethyl)phenyl]methanesulfonamide hydrochloride in 200 mL of methanol, add a solution of 3.04 g of sodium hydroxide in 10 mL of water. Stir for fifteen minutes. Add 11.14 g (0.076 mmol) of 1,2-epoxy-3-phenoxy propane and reflux for 4.5 h. Monitor the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). Remove the solvent in vacuo. Chromatograph the oil on 800 g of silica gel using a mixture of methylene chloride:methanol:triethylamine (97:2:1) initially and changing to methylene chloride, methanol, triethylamine (95:4:1). Combine the fractions containing product and remove the solvent in vacuo. Dissolve the product in methanol and add a solution of hydrogen chloride in methanol. Remove the solvent in vacuo. Recrystallize the salt from acetonitrile:methanol to obtain the title compound.

Workup

  1. temperaturereflux for 4.5 h
  2. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1)
  3. customRemove the solvent in vacuo
  4. additionChromatograph the oil on 800 g of silica gel using a mixture of methylene chloride:methanol:triethylamine (97:2:1) initially
  5. additionCombine the fractions containing product
  6. customremove the solvent in vacuo
  7. dissolutionDissolve the product in methanol
  8. additionadd a solution of hydrogen chloride in methanol
  9. customRemove the solvent in vacuo
  10. customRecrystallize the salt from acetonitrile

Sources & evidence

ORD record
ord-ae02e679a3a641989bef7bc8368e5d32
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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