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

HRID 2263274Notes

Reaction equation

HRID 2263274 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1>C(OCC)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68782766Tert-butyl 4-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate

Product 1

HCID 617805201-[4-(3-Chlorophenyl)-1,3-thiazol-2-yl]piperazineYield 86.8%

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-chlorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate (5.15 g, 13.6 mmol) in ethyl acetate (100 ml), the mixture was stirred at room temperature for 6 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 3.29 g (86.8%) 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-846b2cac05cc4d7aa60560e42d1dbd5c
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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