Water → 2-[(2H-1,3-Benzodioxol-5-yl)amino]ethan-1-ol

HRID 1266185Notes

Reaction equation

HRID 1266185 reaction equation
[C:1]([O-])(=[O:3])[CH3:2].[Na+].BrCCO.[CH2:10]1[O:19][C:18]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=2[O:11]1.O>C(O)C>[CH2:10]1[O:19][C:18]2[CH:17]=[CH:16][C:14]([NH:15][CH2:2][CH2:1][OH:3])=[CH:13][C:12]=2[O:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 843101,3-Benzodioxol-5-amineHCID 517045Sodium Acetate

Product 1

HCID 1755932-[(2H-1,3-Benzodioxol-5-yl)amino]ethan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

27 mmol of sodium acetate and 15 mmol of 2-bromoethanol are added to 10 mmol of 3,4-methylenedioxyaniline dissolved in ethanol. After 24 hours of heating at reflux, the reaction mixture is brought to ambient temperature, water is added, and then the aqueous phase is extracted with dichloromethane. The organic phases are combined, the solvent is evaporated off and the crude residue is purified by chromatography on silica, using a 10:90 dichloromethane/ethyl acetate mixture as eluant, to yield the expected product in the form of an oil.

Workup

  1. temperatureAfter 24 hours of heating
  2. temperatureat reflux
  3. customis brought to ambient temperature
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. customthe solvent is evaporated off
  6. customthe crude residue is purified by chromatography on silica

Sources & evidence

ORD record
ord-056317faa3c64e5daee10c4e9c0514f7
Source dataset
uspto-grants-2003_04
Patent number
US06548515B1

Reaction notes

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