Homoveratrylamine → HCID 3154209, compound

HRID 2114616Notes

Reaction equation

HRID 2114616 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].[CH3:14][C:15]1[O:19][C:18]([CH:20]=O)=[CH:17][CH:16]=1.[BH4-].[Na+]>CCO.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:20][C:18]2[O:19][C:15]([CH3:14])=[CH:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 8421HomoveratrylamineHCID 120975-MethylfurfuralHCID 4311764Sodium borohydride

Product 1

HCID 3154209HCID 3154209, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 4.82 g (26.6 mmol) of 2-(3,4-dimethoxyphenyl)ethylamine and 3.0 g (27.2 mmol) of 5-methylfuran-2-carbaldehyde in 65 ml of EtOH, 18.3 g of molecular sieves (0.3 nm) were added and the mixture was refluxed for 4 hours. After this time the reaction mixture was cooled to room temperature and filtered. The solution obtained was concentrated in vacuo to obtain an oil. This oil was dissolved in 65 ml of MeOH and 1.01 g (26.6 mmol) of NaBH4 were added in small portions, maintaining the temperature of the reaction at room temperature. The mixture was stirred at this temperature for 16 hours more. After this time the solvent was evaporated in vacuo and the residue was treated with 150 ml of water and extracted twice with ether.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. filtrationfiltered
  3. customThe solution obtained
  4. concentrationwas concentrated in vacuo
  5. customto obtain an oil
  6. temperaturemaintaining
  7. customthe temperature of the reaction at room temperature
  8. customAfter this time the solvent was evaporated in vacuo
  9. additionthe residue was treated with 150 ml of water
  10. extractionextracted twice with ether

Sources & evidence

ORD record
ord-14257c35148b4ca4aa8016b1bd3a6c49
Source dataset
uspto-grants-2008_10
Patent number
US07435742B2

Reaction notes

Loading…