Homoveratrylamine → N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 1031988Notes

Reaction equation

HRID 1031988 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].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][C:32](Cl)=[O:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:32](=[O:33])[CH2:31][C:25]2[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride2×

Product 1

HCID 67318N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamideYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

21.7 g of 2-(3,4-dimethoxyphenyl)ethylamine are dissolved in 150 cc of anhydrous chloroform and then the solution is added to 15.2 g of anhydrous triethylamine. The solution is cooled at a temperature between 5° and 10° C. and then, under stirring, there is added the 3,4-dimethoxyphenylacetyl chloride prepared in part (a), 26 g, dissolved in 80 cc of anhydrous chloroform. The temperature is allowed to rise to room temperature. It is then warmed under reflux for eight hours. After cooling the mixture, by addition of an additional portion of chloroform, 200 cc, the organic phase is washed with water and then with 5% hydrochloric acid and an additional amount of water, then 5% sodium hydroxide and finally water. The organic phase is dried over anhydrous sodium sulfate and after filtering, the solvent is evaporated under reduced pressure. The solid thus obtained is recrystallized from absolute ethanol. The pure amide, 36 g, is obtained in a yield of 84%, m.p. 128° C. The substance gives a single spot on chromatography using ethanol as eluent.

Workup

  1. temperatureThe solution is cooled at a temperature between 5° and 10° C.
  2. customto rise to room temperature
  3. temperatureIt is then warmed
  4. temperatureunder reflux for eight hours
  5. temperatureAfter cooling the mixture
  6. washthe organic phase is washed with water
  7. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  8. filtrationafter filtering
  9. customthe solvent is evaporated under reduced pressure
  10. customThe solid thus obtained
  11. customis recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-8967bca04f7248a88f4a46c3ca0ab1c3
Source dataset
uspto-grants-1990_09
Patent number
US04956389

Reaction notes

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