Homoveratrylamine → Stk072897

HRID 1884244Notes

Reaction equation

HRID 1884244 reaction equation
[Cl: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(CC)CC)C>C(OCC)(=O)C.O.O1CCCC1.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]([Cl:1])=[CH:7][CH:6]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

9

Reactant 4

HCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 342164Stk072897Yield 60.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.00 g (29.3 mmol) of (4-chlorophenyl)acetic acid, 5.23 g (43.9 mmol) of thionyl chloride and 50 ml of toluene was stirred at 50° C. for 30 minutes and then 80° C. for 2.5 hours, cooled and concentrated under reduced pressure. The residue was added to a mixture of 5.18 g (28.5 mmol) 2-(3,4-dimethoxyphenyl)ethylamine, 3.46 g (34.2 mmol) of triethylamine and 50 ml tetrahydrofuran at 0° C. and kept at 0° C. for 30 minutes and at room temperature for 3 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 5.75 g of N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-chlorophenyl) acetamide.

Workup

  1. wait80° C. for 2.5 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. waitkept at 0° C. for 30 minutes and at room temperature for 3 hours
  5. customprecipitated solid
  6. filtrationwas collected with filtration
  7. customThe obtained solid was dried

Sources & evidence

ORD record
ord-992752cdd0c542d297781c15bac74d82
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

Loading…