Hydrochloric Acid → N-Acetyl-N-[2-(4-hydroxyphenyl)ethyl]acetamide

HRID 26794Notes

Reaction equation

HRID 26794 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.N1[CH:16]=[CH:15]C=CC=1.[C:17](Cl)(=[O:19])[CH3:18].Cl.[OH2:22]>C1C=CC=CC=1>[C:17]([N:1]([C:15](=[O:22])[CH3:16])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 5610TyramineHCID 6367Acetyl chloride

Product 1

HCID 23470991N-Acetyl-N-[2-(4-hydroxyphenyl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 54.9 g. (0.4 mol) tyramine in 200 ml. pyridine are added dropwise, while stirring at 30°-35° C., 65.8 g. (0.84 mol) acetyl chloride. The reaction mixture is subsequently heated for 15 minutes on a boiling waterbath, then cooled and poured into a mixture of ice and water. By the addition of concentrated hydrochloric acid, it is made markedly acidic and subsequently extracted with chloroform. The chloroform phase is washed with water, dried over anhydrous calcium chloride and then evaporated. There is obtained a residue of 88.5 g. (quantitative yield) of diacetyl-tyramine, which melts at 99°-100° C. after recrystallization from benzene. The diacetyl-tyramine is dissolved in 500 ml. methanol. 800 ml. (0.8 mol) 1 N aqueous potassium hydroxide solution are now added thereto, the temperature thereby increasing to about 30° C., and the mixture is subsequently maintained for 2 hours at an internal temperature of 50° C. It is then cooled, weakly acidified with concentrated hydrochloric acid and the methanol evaporated off in a vacuum. The product which crystallizes out is filtered off with suction, thoroughly washed with water and then dried. There are obtained 58.3 g. (81% of theory) N-acetyl tyramine which, after recrystallization from ethyl acetate, has a melting point of 131° C.

Workup

  1. temperatureThe reaction mixture is subsequently heated for 15 minutes on a boiling waterbath
  2. temperaturecooled
  3. extractionsubsequently extracted with chloroform
  4. washThe chloroform phase is washed with water
  5. dry with materialdried over anhydrous calcium chloride
  6. customevaporated
  7. customThere is obtained a residue of 88.5 g

Sources & evidence

ORD record
ord-71300ed404994ca9a6e386cb2de3c221
Source dataset
uspto-grants-1979_04
Patent number
US04151303

Reaction notes

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