Potassium Iodide → HCID 10957911, compound

HRID 1376176Notes

Reaction equation

HRID 1376176 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]O.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1.[I-].[K+].S(Cl)(Cl)=O.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.CC(C)=O.C(N(CC)CC)C>[N:26]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

10

Reactant 6

HCID 4875Potassium Iodide2×HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 199606-Amino-1-hexanolHCID 24386Thionyl ChlorideHCID 691404-Chloroquinoline

Product 1

HCID 10957911HCID 10957911, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

6-Aminohexanol (15 mmol), 4-chloroquinoline (15 mmol), 5 ml of triethylamine and catalytic amounts of potassium iodide were refluxed in ethanol for 12 hours. The solvent was evaporated and the residue was purified by flash chromatography on silica gel (eluent: methylene chloride/methanol (98/2), ammonia atmosphere). The solvent was removed under reduced pressure. At 0° C. the product (5 mmol) was added to thionyl chloride (10 mmol). The temperature was raised to 70° C. for three hours. Excess thionyl chloride was evaporated. The residue was recrystallized from diethyl ether/ethanol. The product (5 mmol), piperidine (10 mmol), potassium carbonate (15 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 12 hours. The solvent was evaporated and the residue purified by flash chromatography (eluent: ethyl acetate/methanol/triethylamine (95/5/2)). 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/methanol (98/2), ammonia atmosphere)
  3. customThe solvent was removed under reduced pressure
  4. customExcess thionyl chloride was evaporated
  5. customThe residue was recrystallized from diethyl ether/ethanol
  6. customThe solvent was evaporated
  7. customthe residue purified by flash chromatography (eluent: ethyl acetate/methanol/triethylamine (95/5/2))
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-c2422e8b97084295a4b60d2ec4a3d46f
Source dataset
uspto-grants-2007_01
Patent number
US07169928B2

Reaction notes

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