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

HRID 373022Notes

Reaction equation

HRID 373022 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC>[C:12]1([N:8]2[CH2:7][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:27]3[CH2:28][CH2:29][N:24]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)[CH2:25][CH2:26]3)[O:10][C:9]2=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 198115005-(4-Chlorobutyl)-3-phenyl-2-oxazolidinone

Product 1

HCID 198114883-Phenyl-5-[4-[4-(2-pyridinyl)-1-piperazinyl]butyl]-2-oxazolidinoneYield 86%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Following the procedure of Example 5, a mixture of 5-(4-chlorobutyl)-3-phenyl-2-oxazolidinone (3.0 g, 0.01186 mol), 1-(2-pyridinyl)piperazine (1.94 g, 0.01186 mol), potassium carbonate (4.92 g, 0.0356 mol), and potassium iodide (1.0 g) in n-butanol (75 mL) gave an oil, which crystallized upon standing (3.9 g, 86% yield). The solid was recrystallized from isopropanol/isopropyl ether and dried under high vacuum to give 1.80 g, mp 78°-81° C.

Workup

  1. customgave an oil, which
  2. customcrystallized
  3. customThe solid was recrystallized from isopropanol/isopropyl ether
  4. customdried under high vacuum
  5. customto give 1.80 g, mp 78°-81° C.

Sources & evidence

ORD record
ord-18a8835f173b468fb5ae8aabed085787
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

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