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

HRID 2293988Notes

Reaction equation

HRID 2293988 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, and 13.3 g (0.153 mole) of piperazine, 8.4 g (0.061 mole) of potassium carbonate and a catalytic amount of potassium iodide were added thereto. The mixture was refluxed by heating for 5 hours. 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 (the eluent used was a mixture of chloroform:methanol: 28% aqueous ammonia=40:9:1) to obtain 3.62 g of 1-(2-thiazolyl)piperazine as colorless liquid.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureby heating for 5 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additiona mixture of chloroform

Sources & evidence

ORD record
ord-067cdc9de95049fcb135b8e79e54e589
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Reaction notes

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