Homoveratrylamine → HCID 894935, compound

HRID 1884241Notes

Reaction equation

HRID 1884241 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27][NH2:28])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27][NH:28][C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

9

Reactant 4

HCID 8421HomoveratrylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 248474p-Tolylacetic acid

Product 1

HCID 894935HCID 894935, compoundYield 55.2%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5.00 g (33.3 mmol) of (4-methylphenyl)acetic acid, 5.94 g (49.9 mmol) of thionyl chloride, 0.12 g (1.6 mmol) of N,N-dimethylformamide and 20 ml of toluene was stirred at 100° C. for 1 hour, cooled and concentrated under reduced pressure. The residue was added to a mixture of 6.34 g (35.0 mmol) 2-(3,4-dimethoxyphenyl)ethylamine, 8.6 g (67 mmol) of diisopropylethylamine and 25 ml of toluene at 0° C. and kept at 0° C. for 30 minutes and at room temperature for 6 hours. Water and ethyl acetate were added to the reaction mixture and precipitated solid was collected with filtration. The obtained solid was dried to give 5.76 g of N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-methylphenyl)acetamide.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. waitkept at 0° C. for 30 minutes and at room temperature for 6 hours
  4. customprecipitated solid
  5. filtrationwas collected with filtration
  6. customThe obtained solid was dried

Sources & evidence

ORD record
ord-c31a54bd20dc4092939ab9d443bc5683
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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