Triethylamine → HCID 10140955, compound

HRID 1272287Notes

Reaction equation

HRID 1272287 reaction equation
C(N(CC)CC)C.F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.Cl.[CH3:19][C:20]1([CH3:45])[CH:24]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[C:23]2[C:32]([CH3:44])=[C:33]([N:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[C:34]([CH3:37])=[C:35]([CH3:36])[C:22]=2[O:21]1>C(#N)C.C(=O)(O)[O-].[Na+]>[CH3:19][C:20]1([CH3:45])[CH:24]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[C:23]2[C:32]([CH3:44])=[C:33]([N:38]3[CH2:43][CH2:42][N:41]([C:9]4[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=4)[CH2:40][CH2:39]3)[C:34]([CH3:37])=[C:35]([CH3:36])[C:22]=2[O:21]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 22935574HCID 22935574, compound

Product 1

HCID 10140955HCID 10140955, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Triethylamine (0.31 mL, 2.25 mmol) and 4-fluoronitrobenzene (159 μL, 1.5 mmol) were added to a suspension of 1-(2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)piperazine hydrochloride obtained in Example 1 (301 mg, 0.75 mmol) in acetonitrile (6 ml) at room temperature and the mixture was refluxed for 10 hours. The resulting mixture was cooled, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified on silica gel column chromatography (hexane/ethyl acetate=4/1) and crystallized from hexane to obtain 312 mg (yield 86%) of the title compound. mp. 203–205° C. (hexane-ethyl acetate).

Workup

  1. temperaturethe mixture was refluxed for 10 hours
  2. temperatureThe resulting mixture was cooled
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified on silica gel column chromatography (hexane/ethyl acetate=4/1)
  9. customcrystallized from hexane

Sources & evidence

ORD record
ord-7e1dd850efdf49c5ae29055699b1327a
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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