Phenol → HCID 11824896, compound

HRID 722690Notes

Reaction equation

HRID 722690 reaction equation
BrCCCCCCCCBr.[C:11]1(=O)[NH:15][C:14](=O)[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K].[I-].[K+].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.Cl[C:32]1[C:41]2[C:36](=[CH:37][C:38]([Cl:42])=[CH:39][CH:40]=2)[N:35]=[CH:34][CH:33]=1.C1C=CC(O)=CC=1>CC(C)=O>[Cl:42][C:38]1[CH:37]=[C:36]2[C:41]([C:32]([NH:15][CH2:14][CH2:13][CH2:17][CH2:18][CH2:19][CH2:20][CH2:12][CH2:11][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:33][CH:34]=[N:35]2)=[CH:40][CH:39]=1

Participants

8

Reactant 6

HCID 996PhenolHCID 4875Potassium Iodide3×HCID 68664,7-DichloroquinolineHCID 8082PiperidineHCID 783101,8-DibromooctaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 11824896HCID 11824896, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1,8-Dibromooctane (30 mmol), potassium phthalimide (15 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 3 days. The solvent was evaporated, and the residue was purified by flash chromatography on silica gel (eluent: methylene chloride/petroleum ether (60/40)). The solvent was removed under reduced pressure. The product (12,5 mmol), piperidine (50 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 12 hours. Solvent and piperidine were evaporated. The residue was treated with hydrochloric acid (2N), with potassium carbonate solution and was then extracted with methylene chloride. The solvent was removed under reduced pressure, and the residue was refluxed in hydrochloric acid (6N) for 12 hours. The solution was neutralized with potassium carbonate solution and extracted with methylene chloride. The organic layer was evaporated and the product was purified by flash chromatography on silica gel (eluent: methylene chloride/triethylamine/methanol (90/10/2)). The product (5 mmol), 4,7-dichloroquinoline (5 mmol), and catalytic amounts of potassium iodide were melted with 10 g of phenole for 12 hours. The residue was purified by flash chromatography (eluent: ethyl acetate/triethylamine (95/5)). The solvent was removed under reduced pressure. The residue was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography on silica gel (eluent: methylene chloride/petroleum ether (60/40))
  3. customThe solvent was removed under reduced pressure
  4. customSolvent and piperidine were evaporated
  5. additionThe residue was treated with hydrochloric acid (2N), with potassium carbonate solution
  6. extractionwas then extracted with methylene chloride
  7. customThe solvent was removed under reduced pressure
  8. temperaturethe residue was refluxed in hydrochloric acid (6N) for 12 hours
  9. extractionextracted with methylene chloride
  10. customThe organic layer was evaporated
  11. customthe product was purified by flash chromatography on silica gel (eluent: methylene chloride/triethylamine/methanol (90/10/2))
  12. customThe residue was purified by flash chromatography (eluent: ethyl acetate/triethylamine (95/5))
  13. customThe solvent was removed under reduced pressure
  14. customThe residue was crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-f52b345a0b124075a829d39b3be9ebcf
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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