Hydrogen Bromide → HCID 12952720, compound

HRID 1263256Notes

Reaction equation

HRID 1263256 reaction equation
[N:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[CH:2]1.Br>C(O)(=O)C>[N:1]1([N:6]2[CH2:7][CH2:8][N:9]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)[CH2:10][CH2:11]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12952719HCID 12952719, compound

Product 1

HCID 12952720HCID 12952720, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.1 parts of 1-(1H-imidazol-1-yl)-4-(4-methoxyphenyl)piperazine and 150 parts of a hydrobromic acid solution 48% in glacial acetic acid is stirred and refluxed overnight. The reaction mixture is evaporated and the residue is dissolved in water. Upon the addition of an excess of sodium hydrogen carbonate, the product is crystallized. It is filtered off and crystallized again from a mixture of N,N-dimethylformamide and water, yielding 2.8 parts (95%) of 4-[4-(1H-imidazol-1-yl)-1-piperazinyl]phenol; mp. 282.4° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in water
  4. additionUpon the addition of an excess of sodium hydrogen carbonate
  5. customthe product is crystallized
  6. filtrationIt is filtered off
  7. customcrystallized again from a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-71821599a6ca4eafba50106d5b4f8b54
Source dataset
uspto-grants-1984_06
Patent number
US04456605

Reaction notes

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