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

HRID 462008Notes

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

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
  4. extractionextracted twice with 200 parts of ether
  5. customTh solution was dried
  6. distillationUpon distillation

Sources & evidence

ORD record
ord-855d20ea40ee42f0a538e3742a74c975
Source dataset
uspto-grants-1977_12
Patent number
US04064245

Reaction notes

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