tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(4-phenyl-1,3-oxazol-2-yl)piperazine-1-carboxylate

HRID 2262900Notes

Reaction equation

HRID 2262900 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[O:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:19]=1>C1(C)C(C)=CC=CC=1>[C:20]1([C:18]2[N:19]=[C:15]([N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]3)[O:16][CH:17]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 214082612-Chloro-4-phenyloxazole

Product 1

HCID 68777431Tert-butyl 4-(4-phenyl-1,3-oxazol-2-yl)piperazine-1-carboxylateYield 36.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of tert-butyl piperazine-1-carboxylate (1.21 g, 6.51 mmol) and 2-chloro-4-phenyl-1,3-oxazole (390 mg, 2.17 mmol) in xylene (50 ml) was stirred at 155° C. for 12 hours. The solvent was distilled off under reduced pressure. The residue was poured to water, and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1) to give 260 mg (12.1%) of the desired product as a solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionThe residue was poured to water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1)

Sources & evidence

ORD record
ord-d91c89dc96ec4f1cbb566ba1612b675f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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