Potassium Iodide → 3-Methyl-5-(4-Phenyl-1-Piperazinylmethyl)-2-Oxazolidinone

HRID 1533929Notes

Reaction equation

HRID 1533929 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:14][CH:15]1[O:19][C:18](=[O:20])[N:17]([CH3:21])[CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC>[CH3:21][N:17]1[CH2:16][CH:15]([CH2:14][N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)[O:19][C:18]1=[O:20]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 70961-PhenylpiperazineHCID 10340Sodium CarbonateHCID 128899255-(Chloromethyl)-3-methyl-2-oxazolidinone

Product 1

HCID 150300973-Methyl-5-(4-Phenyl-1-Piperazinylmethyl)-2-OxazolidinoneYield 16.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

This compound was prepared according to the procedure of Example 2. A mixture of 3.2 g (0.02 mol) of 1-phenylpiperazine, 3.0 g (0.02 mol) of 5-(chloromethyl)-3-methyl-2-oxazolidinone, 8.0 g (0.075 mol) of anhydrous sodium carbonate, and 0.4 g of potassium iodide in 100 mL of 1-butanol gave a brown oil as residue. The oil was converted to the dioxalate and the solid was recrystallized from acetonitrile-dimethylformamide but did not give a correct combustion analysis. The salt was partitioned between methylene chloride and a 4% sodium hydroxide solution. The organic layer was dried (Na2SO4) and concentrated to yield 0.9 g (16%) of white solid, mp 110°-112° C. (2-propanol).

Workup

  1. customThis compound was prepared
  2. customgave a brown oil as residue
  3. customthe solid was recrystallized from acetonitrile-dimethylformamide
  4. customdid not give a correct combustion analysis
  5. customThe salt was partitioned between methylene chloride
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2ad6af93b3db4b0e8d0bbbbabe3db175
Source dataset
uspto-grants-1992_02
Patent number
US05086055

Reaction notes

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