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

HRID 2198521Notes

Reaction equation

HRID 2198521 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-4be70b23c98c47ce88c1a01ad5a6f55b
Source dataset
uspto-grants-1982_11
Patent number
US04358449

Reaction notes

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