1-Methylpiperazine → 1-Methyl-4-(4-nitro-2-oxazol-2-yl-phenyl)-piperazine

HRID 1910772Notes

Reaction equation

HRID 1910772 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[O:12][CH:13]=[CH:14][N:15]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]2[O:12][CH:13]=[CH:14][N:15]=2)[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 190776092-(2-Chloro-5-nitrophenyl)oxazole

Product 1

HCID 671072361-Methyl-4-(4-nitro-2-oxazol-2-yl-phenyl)-piperazineYield 70%

Procedure

2-(2-Chloro-5-nitrophenyl)-oxazole (0.366 g, 1.63 mmol) was heated in N-methylpiperazine (15 mL) at reflux for 5 hrs. The mixture was allowed to cool and excess N-methylpiperazine was distilled under high vacuum. The residue was diluted with water and extracted with ethyl acetate. The organic phase was washed with water then brine, dried over sodium sulfate, filtered and concentrated. Drying under high vacuum gave 1-methyl-4-(4-nitro-2-oxazol-2-yl-phenyl)-piperazine (0.328 g, 70%) as a solid.

Workup

  1. temperatureat reflux for 5 hrs
  2. temperatureto cool
  3. distillationexcess N-methylpiperazine was distilled under high vacuum
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. dry with materialbrine, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customDrying under high vacuum

Sources & evidence

ORD record
ord-7573a8ef01984a3885c721d010ea6424
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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