HCID 14564861, compound → N-Methylhomoveratrylamine

HRID 1164969Notes

Reaction equation

HRID 1164969 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13](C)[C:14](=O)C(F)(F)F)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>[OH-].[Na+].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 1

HCID 14564861HCID 14564861, compound

Product 1

HCID 77039N-Methylhomoveratrylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 16.5 g (57 mmol) of N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyltrifluoroacetamide in a solution of 100 mL of 4N sodium hydroxide and 100 mL of methanol. Heat mixture at 60° C. for 1 h. After 1 h, cool reaction mixture to room temperature and extract with 2×200 mL of methylene chloride. Wash the combined organic extracts with saturated sodium chloride solution and dry over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to provide the crude title compound. Distill this material in vacuo to provide the title compound.

Workup

  1. temperaturecool
  2. customreaction mixture to room temperature
  3. extractionextract with 2×200 mL of methylene chloride
  4. washWash the combined organic extracts with saturated sodium chloride solution
  5. dry with materialdry over anhydrous sodium sulfate
  6. filtrationFilter the drying agent
  7. customremove the solvent in vacuo
  8. customto provide the crude title compound
  9. distillationDistill this material in vacuo

Sources & evidence

ORD record
ord-383a555e89e84acfa4c193fd581813c6
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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