Potassium Iodide → HCID 23081539, compound

HRID 856281Notes

Reaction equation

HRID 856281 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1([CH3:20])[O:13][C:12]2=[N:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][N:11]2[CH2:10]1)(=O)=O.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C.[I-].[K+]>CN(C=O)C>[CH3:20][C:9]1([CH2:8][CH2:7][CH2:6][N:24]2[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]2)[O:13][C:12]2=[N:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][N:11]2[CH2:10]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23081120HCID 23081120, compound

Product 1

HCID 23081539HCID 23081539, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propyl methane-sulfonate (2 g, 6.6 mmol), tert-butyl piperazine-1-carboxylate (1.4 g, 7.5 mmol), triethylamine (1.3 g, 12.85 mmol), potassium iodide (1.8 g, 10.8 mmol) and DMF (15 ml) was stirred at 60° C. overnight. The reaction mixture was allowed to return to room temperature and then added water, and the resulting solution was extracted with ethyl acetate three times. The organic phases were combined, washed with water twice and then with a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford tert-butyl 4-[3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propyl]piperazine-1-carboxylate (1.9 g, yield 73%) as a white powder.

Workup

  1. customto return to room temperature
  2. extractionadded water, and the resulting solution was extracted with ethyl acetate three times
  3. washwashed with water twice
  4. dry with materialwith a saturated saline solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-bb8de93a08e346ec8cbdcf1a695f6c8d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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