Hydrochloric Acid → 1-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazine

HRID 2263177Notes

Reaction equation

HRID 2263177 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[S:11][CH:12]=1.Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[S:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68782011HCID 68782011, compound

Product 1

HCID 581827331-[4-(2-Fluorophenyl)-1,3-thiazol-2-yl]piperazineYield 94.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution tert-butyl 4-[4-(2-fluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate (3.83 g, 10.5 mmol) in ethyl acetate (100 ml) was added a 4N solution (100 ml) of hydrogen chloride in ethyl acetate, and the mixture was stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in water. The solution was neutralized with 1N aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give the desired product (2.61 g, 94.1%) as an oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionthe mixture was extracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3f4c6ebe69314494bf4d8414eff6690b
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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