Piperazine → 2-(Piperazin-1-yl)-1,3-thiazole-5-carboxylic acid

HRID 80945Notes

Reaction equation

HRID 80945 reaction equation
Br[C:2]1(C(O)=O)[NH:6][CH:5]=[CH:4][S:3]1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:16]([O-])([O-:18])=[O:17].[K+].[K+]>O1CCOCC1>[N:10]1([C:2]2[S:3][C:4]([C:16]([OH:18])=[O:17])=[CH:5][N:6]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 67293743HCID 67293743, compound

Product 1

HCID 672939482-(Piperazin-1-yl)-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Bromothiazole carboxylic acid 1 (1 g; 4.8 mmol) and piperazine (6.2 g; 72 mmol; 24 equiv.) were dissolved in dioxane, K2CO3 (3.32 g; 24 mmol; 5 equiv.) was added and the suspension was refluxed over night. The solvent was removed at the rotary evaporator, the residue dissolved in ethanol, filtered and recrystallized. The crude product was dried at the oil pump and directly used in the following step.

Workup

  1. temperaturethe suspension was refluxed over night
  2. customThe solvent was removed at the rotary evaporator
  3. dissolutionthe residue dissolved in ethanol
  4. filtrationfiltered
  5. customrecrystallized
  6. dry with materialThe crude product was dried at the oil pump

Sources & evidence

ORD record
ord-540876f9926548bb87ef494dd0757107
Source dataset
uspto-grants-2014_09
Patent number
US08846682B2

Reaction notes

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