Methyl iodide → HCID 68418565, compound

HRID 20225Notes

Reaction equation

HRID 20225 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:8][CH2:7][CH2:6][N:5]1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1.[CH3:25]I>CN(C=O)C>[CH3:25][N:8]1[CH2:7][CH2:6][N:5]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:13][CH2:14]2)[C:4]1=[O:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23463818Benzyl 4-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 68418565HCID 68418565, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (80 mg) was added to a solution of benzyl 4-(2-oxoimidazolidin-1-yl)piperidin-1-carboxylate (0.30 g) in DMF (5 mL), the mixture was stirred at room temperature for 30 minutes. After addition of methyl iodide (0.25 mL), the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, diluted with water, and extracted with ethyl acetate. The extract was washed with water, an aqueous 5% citric acid solution and saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (0.32 g, quantitative) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialan aqueous 5% citric acid solution and saturated saline solution and dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ea29079ca2424189abc014472852b2d0
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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