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3-Phenoxyaniline → 1-(3-Phenoxyphenyl)piperazine

HRID 462008
Notes
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Reaction equation

HRID 462008 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.Br.Br[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]Br>>[O:1]([C:8]1[CH:9]=[C:10]([N:11]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 771353-PhenoxyanilineHCID 12692732Bis-(beta-bromoethyl)amine dihydrobromide

Product 1

HCID 184121551-(3-Phenoxyphenyl)piperazine

Procedure

In the manner described in example 1 starting from 49 parts of meta-phenoxyaniline and 83.3 parts of bis-(β-bromoethyl)amine dihydrobromide there was obtained a clear solution. After evaporation of the solvent in vacuo, the residue was treated with 700 part of water, rendered alkaline with 60 parts of concentrated NaOH and extracted twice with 200 parts of ether. Th solution was dried. Upon distillation, there were obtained 26 parts of 1-(3-phenoxyphenyl)-piperazine, B.P./0.5 mm Hg: 180°-190° C.

Workup

  1. customthere was obtained a clear solution
  2. customAfter evaporation of the solvent in vacuo
  3. additionthe residue was treated with 700 part of water
extraction
extracted twice with 200 parts of ether
  • customTh solution was dried
  • distillationUpon distillation
  • Sources & evidence

    ORD record
    ord-855d20ea40ee42f0a538e3742a74c975
    Source dataset
    uspto-grants-1977_12
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04064245

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes