Piperazine → 1-[2-(2,4-Difluoro-phenoxy)-ethyl]-piperazine

HRID 456425Notes

Reaction equation

HRID 456425 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18].C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[O:10][CH2:9][CH2:8][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 232942611-(2-Bromoethoxy)-2,4-difluorobenzene

Product 1

HCID 184370021-[2-(2,4-Difluoro-phenoxy)-ethyl]-piperazineYield 73%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of piperazine (8.7 g, 101.26 mmol) in butanone (70 ml), 4-(2-bromo-ethoxy)-1,3-difluoro benzene (6.0 g, 25.31 mmol), anhydrous K2CO3 (3.5 g, 25.31 mmol) and KI (4.2 g, 25.31 mmol) was refluxed under nitrogen for 18 hours. The mixture was then cooled and filtered and the solvent removed in vacuo. The residue was dissolved in CH2Cl2 (200 ml) and washed with water (50 ml). Drying and removal of the solvent followed by chromatography (CH2Cl2:CH3OH:NH4OH 10:1) afforded desired product in 73% yield.

Workup

  1. temperaturewas refluxed under nitrogen for 18 hours
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2 (200 ml)
  6. washwashed with water (50 ml)
  7. customDrying
  8. customremoval of the solvent

Sources & evidence

ORD record
ord-c1c72bb6d7684682909cb1d87fe96f0c
Source dataset
uspto-grants-2007_03
Patent number
US07186726B2

Reaction notes

Loading…