Veratraldehyde → 134430-93-6

HRID 1823652Notes

Reaction equation

HRID 1823652 reaction equation
[CH:1](=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:13]1([C@H:19]([NH2:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H][H]>C(O)(C)C.[C].[Pd].C(N(CC)CC)C>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH2:1][NH:21][C@@H:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:20]

Participants

7

Reactant 3

HCID 8419VeratraldehydeHCID 6431891-Phenethylamine, (+)-HCID 178418361HCID 178418361, compound

Product 1

HCID 961394134430-93-6Yield 102,264.898%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

Veratraldehyde (174.5 g, 1.05 mole) was dissolved in isopropanol (600 ml) at 10-40° C. and (R)-1-phenylethylamine (121.2 g, 1.00 mmole) was added at 50-60° C. over 1-2 hr in a thin stream. Further, after stirring at 50-60° C. for 1-2 hr, the mixture was cooled to 20° C. To this solution were added triethylamine (5.1 g, 50.0 mmole) and 5% palladium carbon (50% wet, 5.4 g) at 20-30° C. and the mixture was stirred under 1 atm hydrogen atmosphere at 40-45° C. for 7-8 hr. The catalyst was filtered off and the filtrate was concentrated to give the title compound (277.5 g, pure amount 252.5 g, yield 93.05%) (Quantitative analysis by HPLC).

Workup

  1. temperaturethe mixture was cooled to 20° C
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-36b1927f3ce04e32b1f54a667ce3aa3e
Source dataset
uspto-grants-2006_05
Patent number
US07038075B2

Reaction notes

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