Potassium Iodide → HCID 10879264, compound

HRID 1376185Notes

Reaction equation

HRID 1376185 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Br.C1(=O)[NH:17][C:16](=O)[C:15]2=[CH:19][CH:20]=[CH:21]C=C12.[K].[I-].[K+].[NH:27]1CCCCC1>CC(C)=O>[N:17]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:27])[CH2:16][CH2:15][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 4875Potassium Iodide2×HCID 8082PiperidineHCID 2214831,10-DibromodecaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 10879264HCID 10879264, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The synthesis was performed according to the procedure described in example 157 using reagents 1,10-dibromodecane (30 mmol), potassium phthalimide (15 mmol), and catalytic amounts of potassium iodide in the first step. 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 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 final product purified by flash chromatography (eluent: methylene chloride/triethylamine/methanol (90/10/2)). The solvent was removed under reduced pressure. The residue was crystallized with oxalic acid from diethyl ether/ethanol.

Workup

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

Sources & evidence

ORD record
ord-de42279ccd184a09916d1a74d33f901a
Source dataset
uspto-grants-2007_01
Patent number
US07169928B2

Reaction notes

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