Potassium Iodide → 1-{2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperid-1-yl]ethyl}imidazolidin-2-one

HRID 1956352Notes

Reaction equation

HRID 1956352 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].[F:10][C:11]1[CH:25]=[CH:24][C:14]2[C:15]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:16][O:17][C:13]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C(C)C>[F:10][C:11]1[CH:25]=[CH:24][C:14]2[C:15]([CH:18]3[CH2:19][CH2:20][N:21]([CH2:2][CH2:3][N:4]4[CH2:8][CH2:7][NH:6][C:5]4=[O:9])[CH2:22][CH2:23]3)=[N:16][O:17][C:13]=2[CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 754351-(2-Chloroethyl)imidazolidin-2-oneHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 110996181-{2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperid-1-yl]ethyl}imidazolidin-2-oneYield 61.9%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

21.4 g (0.144 mol) of 1-(2-chloroethyl)imidazolidin-2-one, 23.6 g (0.107 mol) of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine, 92.9 g (0.67 mol) of potassium carbonate, 2.6 g of potassium iodide and 524 ml of methyl isobutyl ketone are placed in a three-necked flask. Refluxing is carried out for one night, and then the reaction mixture is concentrated and taken up in a mixture of water/ethyl acetate. Decanting is carried out, and the organic phase is washed several times with water and then extracted with a normal solution of hydrochloric acid. The acidic phase is then rendered basic with sodium hydroxide solution and extracted with methylene chloride. Drying is carried out over MgSO4. After evaporation, the residue is recrystallised from 80 ml of acetonitrile to yield 22 g of a solid that corresponds to the expected product. M.p.=137°-141° C. (Yield=46%).

Workup

  1. temperatureRefluxing
  2. waitis carried out for one night
  3. concentrationthe reaction mixture is concentrated
  4. additiontaken up in a mixture of water/ethyl acetate
  5. customDecanting
  6. washthe organic phase is washed several times with water
  7. extractionextracted with a normal solution of hydrochloric acid
  8. extractionextracted with methylene chloride
  9. customDrying
  10. customAfter evaporation
  11. customthe residue is recrystallised from 80 ml of acetonitrile

Sources & evidence

ORD record
ord-5ba829aecc56441bb61d08a55b0a0d5b
Source dataset
uspto-grants-1998_07
Patent number
US05780474

Reaction notes

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