Potassium Iodide → HCID 18539103, compound

HRID 412905Notes

Reaction equation

HRID 412905 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.[I-].[K+].[N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][CH:23]=1.[H-].[Na+]>CN(C)C=O.O>[N:22]1([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Product 1

HCID 18539103HCID 18539103, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

t-Butyl 4-methylsulfonyloxymethyl-1-piperidinecarboxylate (0.50 g, 1.7 mmol) was dissolved in dimethylformamide (8 ml). To the solution were added potassium iodide (0.37 g), benzimidazole (0.26 g) and 60% sodium hydride in mineral oil (0.088 g), successively, and the mixture was stirred at 60° C. for 2 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with water three times, dried over magnesium sulfate and concentrated under reduced pressure. The resulting solid materials were recrystallized from ethyl acetate/hexane to give the titled compound (0.45 g, 1.4 mmol, Yield 82%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washThe organic layer was washed with water three times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solid materials were recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9892fb355d3a496ba7138b44cbbe2183
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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