Tyramine → 4-Vinylacetamidoethyl phenol

HRID 968884

Reaction equation

HRID 968884 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH:18]([CH2:20][C:21](Cl)=[O:22])=[CH2:19]>C(Cl)Cl>[CH:18]([CH2:20][C:21]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:22])=[CH2:19]

Participants

5

Reactant 3

HCID 5610TyramineHCID 8471TriethylamineHCID 10975427But-3-enoyl Chloride

Product 1

HCID 626796864-Vinylacetamidoethyl phenolYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1000 mL 3-neck, round bottom flask connected with a reflux condenser and a drying tube, is charged with 250 mL of methylene chloride, 5.48 grams (0.04 mole) 4-aminoethylphenol and 4.04 grams (0.04 mole) triethylamine. The contents are chilled with an ice bath. Through a dropping funnel, 4.18 grams (0.04 mole) of vinylacetyl chloride is added into the flask over a period of 30 minutes. The ice bath is then removed and the contents are continuously stirred overnight. The mixture is then filtered and then condensed using a rotavapor. HPLC analysis indicates only one major product. The product is then passed through silica gel chromatography to give a final purified product with a yield of at least 80 percent. The product is identified by NMR and Mass Spectroscopy.

Workup

  1. customA 1000 mL 3-neck, round bottom flask connected with a reflux condenser and a drying tube
  2. temperatureThe contents are chilled with an ice bath
  3. customThe ice bath is then removed
  4. filtrationThe mixture is then filtered
  5. customcondensed
  6. customto give
  7. customa final purified product with a yield of at least 80 percent

Sources & evidence

ORD record
ord-10238c376db34c5086dacc7c295f9e36
Source dataset
uspto-grants-2007_12
Patent number
US07304117B2

Linked notes

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