Potassium Iodide → HCID 11192494, compound

HRID 1376182Notes

Reaction equation

HRID 1376182 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[I-].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27].[Cl-].[Cl-].[Cl-].[Al+3].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[N+](C1C=CC=CC=1)([O-])=O.C(OCC)(=O)C>[N:12]1([CH2:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

10

Reactant 6

HCID 4875Potassium Iodide2×HCID 8082Piperidine2×HCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 898486-Bromohexanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11192494HCID 11192494, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 7416NitrobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Phenoxypropylbromide (10 mmol), piperidine (20 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 12 hours. The solvent was evaporated. The residue was treated with ethyl acetate. The solvent was removed under reduced pressure, and the product was crystallized with hydrochloric acid from isopropanol/diethyl ether. The product (5 mmol) was added to a solution of 6-bromohexanoylchloride (7.5 mmol) and aluminiumtrichloride (22.5 mmol) in 10 ml of nitrobenzol. The mixture was stirred at room temperature for 3 days. Ethyl acetate was added, and the mixture was extracted with hydrochloric acid (6N). The solution was neutralized with potassium carbonate solution and extracted with methylene chloride. The solvent was removed under reduced pressure. The product (2.5 mmol), piperidine (5 mmol), potassium carbonate (7.5 mmol), and catalytic amounts of potassium iodide were refluxed in acetone for 12 hours. The solvent was evaporated, and the residue was purified by flash chromatography (eluent: methylene chloride/petroleum ether/methanol (96/3/3)). 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. additionThe residue was treated with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customthe product was crystallized with hydrochloric acid from isopropanol/diethyl ether
  5. extractionthe mixture was extracted with hydrochloric acid (6N)
  6. extractionextracted with methylene chloride
  7. customThe solvent was removed under reduced pressure
  8. customThe solvent was evaporated
  9. customthe residue was purified by flash chromatography (eluent: methylene chloride/petroleum ether/methanol (96/3/3))
  10. customThe solvent was removed under reduced pressure
  11. customThe residue was crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-32ba439cf824436badd62bb5c0f36056
Source dataset
uspto-grants-2007_01
Patent number
US07169928B2

Reaction notes

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