Acetic Anhydride → 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone

HRID 614429

Reaction equation

HRID 614429 reaction equation
Br.Br.[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:16]([N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 2723591p-(1-Piperazinyl)phenol dihydrobromide

Product 1

HCID 7124411-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 33.8 parts of 4-(1-piperazinyl)phenol dihydrobromide, 11.2 parts of acetic acid anhydride, 42 parts of potassium carbonate and 300 parts of 1,4-dioxane is stirred and refluxed for 3 days. The reaction mixture is filtered and the filtrate is evaporated. The solid residue is stirred in water and sodium hydrogen carbonate is added. The whole is stirred for 30 minutes. The precipitated product is filtered off and dissolved in a diluted hydrochloric acid solution. The solution is extracted with trichloromethane. The acid aqueous phase is separated and neutralized with ammonium hydroxide. The product is filtered off and crystallized from ethanol, yielding 5.7 parts of 1-acetyl-4-(4-hydroxyphenyl)piperazine; mp. 181.3° C.

Workup

  1. temperaturerefluxed for 3 days
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. stirringThe solid residue is stirred in water
  5. additionsodium hydrogen carbonate is added
  6. stirringThe whole is stirred for 30 minutes
  7. filtrationThe precipitated product is filtered off
  8. dissolutiondissolved in a diluted hydrochloric acid solution
  9. extractionThe solution is extracted with trichloromethane
  10. customThe acid aqueous phase is separated
  11. filtrationThe product is filtered off
  12. customcrystallized from ethanol

Sources & evidence

ORD record
ord-056bb84148764c28ad88c8ee0dbb26cc
Source dataset
uspto-grants-1979_03
Patent number
US04144346

Linked notes

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