Hydrochloric Acid → 5-Methyl-4-phenyl-2-piperazinyl-1,3-thiazole

HRID 2263170Notes

Reaction equation

HRID 2263170 reaction equation
C(ONC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]([CH3:26])=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[CH3:26][C:17]1[S:16][C:15]([N:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)=[N:19][C:18]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86625508N-(tert-butoxy)-4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

Product 1

HCID 172338685-Methyl-4-phenyl-2-piperazinyl-1,3-thiazoleYield 85.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of N-(tert-butoxy)-4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide (2.45 g, 6.82 mmol) in ethyl acetate (200 ml) was added a 4N hydrogen chloride solution in ethyl acetate (40 ml), and the mixture was stirred at room temperature for 18 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in water. The solution was neutralized with 1N sodium hydroxide, 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 1.51 g (85.6%) of the desired product 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-e67e7140855e4fe48221a0e00bfd05b8
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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