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

HRID 2263305Notes

Reaction equation

HRID 2263305 reaction equation
Cl.[CH3:2][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>[CH3:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[S:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68778457HCID 68778457, compound

Product 1

HCID 617815611-[4-(3-Methylphenyl)-1,3-thiazol-2-yl]piperazineYield 63.1%

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-methylphenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate (2.00 g, 5.56 mmol) in ethyl acetate (50 ml), 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 910 mg (62.9%) 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-9080338f40fb469192b55ba9bcb7a7c4
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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