Benzaldehyde → N-Methylhomoveratrylamine

HRID 1451637Notes

Reaction equation

HRID 1451637 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:14](=O)C1C=CC=CC=1.CI>C(O)C>[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

5

Reactant 3

HCID 240BenzaldehydeHCID 6328Methyl iodideHCID 8421Homoveratrylamine

Product 1

HCID 77039N-MethylhomoveratrylamineYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dimethoxybenzeneethanamine (100 g) was mixed with benzaldehyde (59 g), and rotoevaporated to give an oil. Methyl iodide (69 ml) was then added and the mixture was heated for 48 h at 40° and then boiled with 80% ethanol (500 ml) for 3 h. After half of the ethanol had evaporated, the solution was treated with ether (1 liter) to give a solid that was filtered, washed with ether, treated with dilute sodium hydroxide and extracted with ether to give the title compound (80 g) as an oil that was distilled under reduced pressure, b.p. 0.1 mm; 92°-95°.

Workup

  1. customto give an oil
  2. temperaturethe mixture was heated for 48 h at 40°
  3. customAfter half of the ethanol had evaporated
  4. additionthe solution was treated with ether (1 liter)
  5. customto give a solid
  6. filtrationthat was filtered
  7. washwashed with ether
  8. additiontreated with dilute sodium hydroxide
  9. extractionextracted with ether

Sources & evidence

ORD record
ord-6d34a0445966402ba764db1a2d0a5e66
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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