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

HRID 490166Notes

Reaction equation

HRID 490166 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 87.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The procedure described in J. Med. Chem 1996, 39(7), 1431 was followed to provide the title compound. A mixture of 2-bromothiazole (3 g, 18.3 mmol) and piperazine (3.15 g, 36.6 mmol) was refluxed in n-butanol for 18 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was treated with an aqueous solution of 10% K2CO3 and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and the filtrate concentrated under reduced pressure to provide 2.7 g (87%) of the title compound as brown oil used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 2.99 (m, 4H), 3.47 (m, 4H), 6.57 (d, 1H, J=4.5 Hz), 7.20 (d, 1H, J=4.5 Hz); MS (DCI/NH3) m/e 170 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with an aqueous solution of 10% K2CO3
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-847bbd03c42d49a8a0485133ae091f67
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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