Piperazine → Ethyl 2-(piperazin-1-yl)-1,3-thiazole-5-carboxylate

HRID 1594003Notes

Reaction equation

HRID 1594003 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C(O)C>[N:12]1([C:2]2[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 54595879Ethyl 2-(piperazin-1-yl)-1,3-thiazole-5-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.02 g (5.0 mmol) of ethyl 2-bromothiazole-5-carboxylate and 4.31 g (50 mmol) of piperazine were dissolved in ethanol (20 ml) and the mixture was heated under reflux over a period of 4 h. The solution was then concentrated in vacuo, taken up in EA and washed successively with water and a satd aq. NaCl solution. Following drying of the organic phase over MgSO4, filtration and removal of solvent in vacuo there were obtained 1.12 g (4.6 mmol, 93%) of ethyl 2-piperazin-1-ylthiazole-5-carboxylate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux over a period of 4 h
  3. concentrationThe solution was then concentrated in vacuo
  4. washwashed successively with water
  5. dry with materialFollowing drying of the organic phase over MgSO4, filtration and removal of solvent in vacuo

Sources & evidence

ORD record
ord-6b095b5db6f74b3ab4a55b43fd34cf20
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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