Sodium Iodide → 1-(2-Chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethylphenoxy)piperidin-1-yl]propan-2-ol

HRID 856245Notes

Reaction equation

HRID 856245 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][C:11]([OH:25])([CH3:24])[CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[F:26][C:27]([F:42])([F:41])[C:28]1[CH:40]=[CH:39][C:31]([O:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:30][CH:29]=1.[I-].[Na+].C(N(CC)CC)C>CN(C=O)C.O>[Cl:1][C:2]1[N:3]([CH2:10][C:11]([CH3:24])([OH:25])[CH2:12][N:36]2[CH2:35][CH2:34][CH:33]([O:32][C:31]3[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:41])[F:42])=[CH:40][CH:39]=3)[CH2:38][CH2:37]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 36883924-(4-(Trifluoromethyl)phenoxy)piperidineHCID 230812352-Chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole

Product 1

HCID 230811331-(2-Chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethylphenoxy)piperidin-1-yl]propan-2-olYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-1-[2-hydroxy-2-methyl-3-(4-methylbenzenesulfonyloxy)propyl]-4-nitroimidazole prepared in Example 5 (0.30 g, 0.77 mmol) and 4-(4-trifluoromethylphenoxy)piperidine (0.21 g, 0.85 mmol) in DMF (6 ml), sodium iodide (0.13 g, 0.77 mmol) and triethylamine (0.12 ml, 0.77 mmol) were added followed by stirring at 80° C. for 7 hours. To the reaction mixture, water was added, and the resulting solution was extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford 1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethylphenoxy)piperidin-1-yl]propan-2-ol (0.23 g, yield 63%) as a yellow oil.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-8e7ae3ecb05f4cca8e7e9c918ff1cf65
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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