Hydrochloric Acid → 1-(4-Phenyl-1,3-oxazol-2-yl)piperazine

HRID 2262901Notes

Reaction equation

HRID 2262901 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>O1CCCC1.CO.C(OCC)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68777431Tert-butyl 4-(4-phenyl-1,3-oxazol-2-yl)piperazine-1-carboxylate

Product 1

HCID 687757351-(4-Phenyl-1,3-oxazol-2-yl)piperazineYield 90.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(4-phenyl-1,3-oxazol-2-yl)piperazine-1-carboxylate (590 mg, 1.79 mmol) in tetrahydrofuran (4 ml) and methanol (4 ml) was added a solution of 4 N hydrogen chloride in ethyl acetate (4 ml), and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure. The residue was poured to an aqueous 1 N sodium hydroxide solution (10 ml) and extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 370 mg (90.0%) of the desired product as an oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionThe residue was poured to an aqueous 1 N sodium hydroxide solution (10 ml)
  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-27bd0f892f104f3793209c30ee1a4cde
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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