Piperazine → 1-(Thiazol-2-yl)piperazine

HRID 1636283Notes

Reaction equation

HRID 1636283 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[NH3:6].[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 764302-Bromothiazole

Product 2

HCID 222AmmoniaYield 28%HCID 9118061-(Thiazol-2-yl)piperazineYield 140.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 50 ml of acetonitrile was dissolved 5.0 g (0.0305 mole) of 2-bromothiazole, then, 13.1 g (0.153 mole) of piperazine, 8.4 g (0.061 mole) of potassium carbonate and a catalytic amount of potassium iodide were added to the solution, and the mixture was refluxed under heating for 5 hours. After the mixture was cooled to room temperature and then filtered, the filtrate was concentrated under reduced pressure, and the residue was applied to silica gel column chromatography (eluent; a chloroform:methanol:28% aqueous ammonia=40:9:1 mixed solution) to obtain 3.62 g of 1-(2-thiazolyl)piperazine as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 hours
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5e6d32a15822492298e05cb8783b4137
Source dataset
uspto-grants-2000_03
Patent number
US06034086

Reaction notes

Loading…