Isobutylene oxide → HCID 63239148, compound

HRID 2036180Notes

Reaction equation

HRID 2036180 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22]1([O:25][CH2:24]1)[CH3:23]>C(#N)C>[OH:25][C:22]([CH3:24])([CH3:23])[CH2:21][N:12]1[CH2:13][CH2:14][N:9]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 7626541-Benzoylpiperazine

Product 1

HCID 63239148HCID 63239148, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

500 mg (2.63 mmol) 1-benzoylpiperazine and 1.10 g (7.96 mmol, 3.0 eq.) potassium carbonate were suspended to 20 ml acetonitrile at room temperature. After adding 570 mg (7.90 mmol, 3.0 eq.) isobutylene oxide, it was heated at reflux and stirred overnight. After cooling to room temperature and adding 30 ml purified water, it was extracted twice with 30 ml ethylacetate. After collecting organic layer and drying with anhydrous magnesium sulfate, it was concentrated with decompression. The obtained residue was purified by chromatography using silicagel (mobile phase: dichloromethane/methanol=20:1) and 276 mg (40%) target compound as light-yellow solid was yielded.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. additionadding 30 ml
  4. custompurified water, it
  5. extractionwas extracted twice with 30 ml ethylacetate
  6. customAfter collecting organic layer
  7. dry with materialdrying with anhydrous magnesium sulfate, it
  8. concentrationwas concentrated with decompression
  9. customThe obtained residue was purified by chromatography
  10. custom276 mg (40%) target compound as light-yellow solid was yielded

Sources & evidence

ORD record
ord-4dc28ac386754abbba8c7e69549da59d
Source dataset
uspto-grants-2013_11
Patent number
US08575173B2

Reaction notes

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