Hydrogen Bromide → 4-[4-(4-Aminophenyl)piperazin-1-yl]phenol

HRID 1154748

Reaction equation

HRID 1154748 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br>O>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)[CH2:10][CH2:11]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 154406Benzenamine, 4-(4-(4-methoxyphenyl)-1-piperazinyl)-

Product 1

HCID 102210654-[4-(4-Aminophenyl)piperazin-1-yl]phenolYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 parts of 4-[4-(4-methoxyphenyl)-1-piperazinyl]benzenamine and 300 parts of a hydrobromic acid solution 48% in water is stirred and refluxed for 10 days. The reaction mixture is evaporated and the residue is alkalized with sodium hydroxide. The mixture is filtered and the filtrate is acidified with acetic acid. The precipitated product is filtered off and crystallized from 1,4-dioxane, yielding 12 parts (44%) of 4-[4-(4-aminophenyl)-1-piperazinyl]phenol.

Workup

  1. temperaturerefluxed for 10 days
  2. customThe reaction mixture is evaporated
  3. filtrationThe mixture is filtered
  4. filtrationThe precipitated product is filtered off
  5. customcrystallized from 1,4-dioxane

Sources & evidence

ORD record
ord-476e78f0e2374da3afda6f1c0fbd12bb
Source dataset
uspto-grants-1984_12
Patent number
US04490530

Linked notes

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