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

HRID 2263182Notes

Reaction equation

HRID 2263182 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68777432HCID 68777432, compound

Product 1

HCID 617813921-[4-(3-Fluorophenyl)-1,3-thiazol-2-yl]piperazineYield 86.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl 4-[4-(3-fluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate (780 mg, 2.15 mmol) in ethyl acetate (50 ml) was added a 4N solution (25 ml) of hydrogen chloride in ethyl acetate, and the mixture was stirred at room temperature for 14 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 (487 mg, 86.3%) as a solid.

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-98073b4a60364d07959be2f7ef6408ee
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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