Potassium Iodide → HCID 21883828, compound

HRID 722685Notes

Reaction equation

HRID 722685 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Br)=[CH:5][CH:4]=1.[CH3:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH3:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.[I-].[K+]>CC(C)=O>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][N:31]3[CH2:32][CH2:33][CH:28]([CH3:27])[CH2:29][CH2:30]3)=[CH:5][CH:4]=2)=[CH:16][CH:15]=1)(=[O:13])[CH3:11]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 74694'-HydroxyacetophenoneHCID 11430Potassium Carbonate2×HCID 693351,4-Bis(bromomethyl)benzeneHCID 693814-Methylpiperidine

Product 1

HCID 21883828HCID 21883828, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

α,α′-Dibromo-para-xylene (30 mmol), 4-hydroxyacetophenone (20 mmol), and potassium carbonate (50 mmol) were refluxed in 50 ml of acetone for 12 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel (eluent: methylene chloride/petroleum ether/methanol (60/38/2)). The product (2 mmol), 4-methylpiperidine (6 mmol), potassium carbonate (8 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 12 hours. The solvent was evaporated. The residue was washed with water and extracted with ethyl acetate. The solvent was removed under reduced pressure. The product was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography on silica gel (eluent: methylene chloride/petroleum ether/methanol (60/38/2))
  3. customThe solvent was evaporated
  4. washThe residue was washed with water
  5. extractionextracted with ethyl acetate
  6. customThe solvent was removed under reduced pressure
  7. customThe product was crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-f157ccc62ded4188a1b987ab0f56ebbb
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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