Triethylamine → 2-(4-Cyclopropylpiperazin-1-yl)benzooxazole-5-carbonitrile

HRID 1944698Notes

Reaction equation

HRID 1944698 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1.CCN(CC)CC.[CH:20]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][CH2:21]1>CCO>[CH:20]1([N:23]2[CH2:28][CH2:27][N:26]([C:2]3[O:3][C:4]4[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=4[N:6]=3)[CH2:25][CH2:24]2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 47420041-CyclopropylpiperazineHCID 106311802-Chloro-5-benzoxazolecarbonitrile

Product 1

HCID 237288972-(4-Cyclopropylpiperazin-1-yl)benzooxazole-5-carbonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chlorobenzooxazole-5-carbonitrile (1.69 g, 9.5 mmol) in EtOH (34 mL) was added Et3N (4.8 g, 47.5 mmol), followed by 1-cyclopropylpiperazine (1.44 g, 11.4 mmol) and the mixture was heated at reflux for 12 h. Then the volatiles were evaporated to remove EtOH and water (120 mL) was added. The mixture was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (elute: 10% ethyl acetate in petroleum ether, 0.1% NH4OH added) to give 1.34 g (53%) of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carbonitrile.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThen the volatiles were evaporated
  4. customto remove EtOH and water (120 mL)
  5. additionwas added
  6. extractionThe mixture was extracted with CH2Cl2 (3×50 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel (elute: 10% ethyl acetate in petroleum ether, 0.1% NH4OH added)

Sources & evidence

ORD record
ord-aa8233b9da7f4265bbc147efa997d843
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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