3-Methoxytyramine → 2-(4-Chlorophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

HRID 2112294Notes

Reaction equation

HRID 2112294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(C)(C)O[C:9]2=[O:15])=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[C:9]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=2)=[O:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 16693-MethoxytyramineHCID 10775653HCID 10775653, compound

Product 1

HCID 179554462-(4-Chlorophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-(4-Chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-one (5.67 g; 25 mmol) and 4-(2-aminoethyl)-2-methoxyphenol (4.39 g; 26.25 mmol) are dissolved in 31.25 g of dry dioxane. The mixture is heated to reflux (+100° C.) and the solution is stirred for 7 hours at reflux temperature. The solvent is removed in vacuum and to the residue 20 g of a 1:1 mixture of ethyl acetate and hexane is added at +70° C. whereupon a precipitate is formed. After cooling, filtering and washing the product is dried in vacuum. 7.44 g of 2-(4-chlorophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-acetamide with a purity of 91.0% is obtained in 80.6% yield.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux (+100° C.)
  3. temperatureat reflux temperature
  4. customThe solvent is removed in vacuum and to the residue 20 g of a 1:1 mixture of ethyl acetate and hexane
  5. additionis added at +70° C. whereupon a precipitate
  6. customis formed
  7. temperatureAfter cooling
  8. filtrationfiltering
  9. washwashing the product
  10. customis dried in vacuum

Sources & evidence

ORD record
ord-9ceaee71e28c4db0872637c4b8ae69c4
Source dataset
uspto-grants-2009_04
Patent number
US07521579B2

Reaction notes

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