Potassium Iodide → 3-Methyl-5-[4-(4-phenyl-1-piperazinyl)butyl]-2-oxazolidinone

HRID 373012Notes

Reaction equation

HRID 373012 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([CH3:12])[CH2:7]1.Cl.[C:14]1([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC>[CH3:12][N:8]1[CH2:7][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:23]2[CH2:24][CH2:25][N:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:21][CH2:22]2)[O:10][C:9]1=[O:11]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 751641-Phenylpiperazinium chlorideHCID 198114625-(4-Chlorobutyl)-3-methyl-2-oxazolidinone

Product 1

HCID 99269853-Methyl-5-[4-(4-phenyl-1-piperazinyl)butyl]-2-oxazolidinoneYield 45%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 5-(4-chlorobutyl)-3-methyl-2-oxazolidinone (10.0 g, 0.0524 mol), 1-phenylpiperazine hydrochloride (0.0524 mol, 10.39 g), potassium carbonate (28.94 g, 0.209 mol) and potassium iodide (1.0 g) was refluxed in 1-butanol (150 mL) for 24 hr and then stirred at room temperature for two days. The mixture was reheated to boiling and filtered hot. Methanolic hydrogen chloride was added to acidify the filtrate and addition of isopropyl ether caused a solid to precipitate. The solid was collected by filtration and dissolved in water. Potassium carbonate was added to make the solution basic and the product was extracted into two portions of ethyl acetate. The combined ethyl acetate layers were washed twice with water, three times with a saturated sodium bicarbonate solution and once with a saturated sodium chloride solution. The solution was dried (sodium sulfate), filtered, and evaporated under reduced pressure to an oil. Addition of isopropyl ether gave a solid which was recrystallized from isopropyl ether/methanol. The solid was collected by filtration, rinsed with light pet ether and dried under high vacuum to give 7.51 g (45% yield), mp 85°-88° C.

Workup

  1. filtrationfiltered hot
  2. additionMethanolic hydrogen chloride was added
  3. additionthe filtrate and addition of isopropyl ether
  4. customto precipitate
  5. filtrationThe solid was collected by filtration
  6. dissolutiondissolved in water
  7. additionPotassium carbonate was added
  8. extractionthe product was extracted into two portions of ethyl acetate
  9. washThe combined ethyl acetate layers were washed twice with water, three times with a saturated sodium bicarbonate solution and once with a saturated sodium chloride solution
  10. dry with materialThe solution was dried (sodium sulfate)
  11. filtrationfiltered
  12. customevaporated under reduced pressure to an oil
  13. additionAddition of isopropyl ether
  14. customgave a solid which
  15. customwas recrystallized from isopropyl ether/methanol
  16. filtrationThe solid was collected by filtration
  17. washrinsed with light pet ether
  18. customdried under high vacuum
  19. customto give 7.51 g (45% yield), mp 85°-88° C.

Sources & evidence

ORD record
ord-87ff04457fcc4d198d001196dae5b14d
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

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