Potassium Iodide → 5-[2-[4-(4-Fluorophenyl)-1-piperazinyl]ethyl]-3-methyl-2-oxazolidinone

HRID 1533908Notes

Reaction equation

HRID 1533908 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][CH:17]1[O:21][C:20](=[O:22])[N:19]([CH3:23])[CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH:17]3[O:21][C:20](=[O:22])[N:19]([CH3:23])[CH2:18]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 146987465-(2-Chloro-ethyl)-3-methyl-oxazolidin-2-one

Product 1

HCID 150300685-[2-[4-(4-Fluorophenyl)-1-piperazinyl]ethyl]-3-methyl-2-oxazolidinoneYield 74.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4.5 g (0.025 mol) of 1-(4-fluorophenyl)piperazine, 4.1 g (0.025 mol) of 5-(2-chloroethyl)-3-methyl-2-oxazolidinone, 8.0 g (0.075 mol) of anhydrous sodium carbonate and 0.4 g of potassium iodide in 150 mL of n-butanol was heated at reflux for 20 h. The mixture was concentrated under reduced pressure and the residue partitioned between water and benzene. The benzene layer was washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure to obtain a solid which was recrystallized from 2-propanol isopropyl/ether to obtain 5.7 g (74%) of white solid, mp 82°-84° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between water and benzene
  5. washThe benzene layer was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customto obtain a solid which
  9. customwas recrystallized from 2-propanol isopropyl/ether

Sources & evidence

ORD record
ord-fe13c0c363db478ea9ec6d2ff476f63a
Source dataset
uspto-grants-1992_02
Patent number
US05086055

Reaction notes

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