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

HRID 2263299Notes

Reaction equation

HRID 2263299 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1>C(OCC)(=O)C>[F:29][C:3]([F:2])([F:28])[C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68780226HCID 68780226, compound

Product 1

HCID 617810421-[4-(3-Trifluoromethylphenyl)-1,3-thiazol-2-yl]piperazineYield 47.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 4 N solution (50 ml) of hydrogen chloride in ethyl acetate was added to a solution of tert-butyl 4-[4-(3-trifluoromethylphenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate (1.85 g, 4.74 mmol) in ethyl acetate (50 ml), an the mixture was stirred at room temperature for 12 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in water, neutralized with a 1 N sodium hydroxide aqueous solution, and 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 678 mg (47.9%) of the desired product as an oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted 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-e0ccf1413d594e65b31f37052eacf3cf
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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