Hydrochloric Acid → N-Acetyltyramine

HRID 275897Notes

Reaction equation

HRID 275897 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:9][CH:8]=1)(=O)C.Cl>O.CO>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 577423N,O-Diacetyltyramine

Product 1

HCID 121051N-AcetyltyramineYield 84.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide(2.3 g, 58 mmol) in water(20 ml) was cooled to 0° C. A solution of N-(4-acetoxyphenylethyl)acetamide(6.4 g, 29 mmol) in methanol(40 ml) was added dropwise to the soultion, stirred for 10 minutes, adjusted to pH 1 with hydrochloric acid, and then extracted 3 times with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting oily residue was solidified with ethyl ether, filtered, and dried to give 4.4 g of the titled compound.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-a0b6ce5ef7a04bb3bf16b305f975a3ce
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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