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

HRID 1593997Notes

Reaction equation

HRID 1593997 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)CCC>[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

4

Reactant 2

HCID 4837PiperazineHCID 764302-Bromothiazole

Product 1

HCID 9118061-(Thiazol-2-yl)piperazineYield 28.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

3.61 g (22.0 mmol) of 2-bromothiazole were dissolved in n-butanol (20 ml) together with 1.90 g (22.0 mmol) piperazine. The reaction solution was heated at 120° C. 3 h and stirred at RT a further 16 h. The precipitate formed was then filtered off and the filtrate was concentrated in vacuo. The residue was taken up in DCM, and a 1 M aq. sodium carbonate soln was added. After separation of the phases, the organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. A column chromatography (MeOH:DIPE 1:1) was carried out on the residue to give 1.06 g (6.3 mmol, 28% of theory) of 1-thiazol-2-ylpiperazine.

Workup

  1. customThe precipitate formed
  2. filtrationwas then filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. additiona 1 M aq. sodium carbonate soln was added
  5. customAfter separation of the phases
  6. dry with materialthe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b2637a748db472791186dbacfadbfd7
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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