Methyl iodide → HCID 57495300, compound

HRID 242303Notes

Reaction equation

HRID 242303 reaction equation
[N:1]1([C:7](=[O:9])[CH3:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C1N=CN([C:15]([N:17]2[CH:21]=[N:20][CH:19]=[CH:18]2)=[O:16])C=1.[CH3:22][I:23]>C1COCC1.C(Cl)Cl.O.C(#N)C>[I-:23].[C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:15]([NH+:17]2[CH:18]=[CH:19][N:20]([CH3:22])[CH2:21]2)=[O:16])[CH2:3][CH2:2]1)(=[O:9])[CH3:8]

Participants

8

Reactant 3

HCID 6328Methyl iodideHCID 682631,1'-CarbonyldiimidazoleHCID 837951-Acetylpiperazine

Product 1

HCID 57495300HCID 57495300, compoundYield 97.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(piperazin-1-yl)ethanone (143 mg, 1.12 mmol) and CDI (199 mg, 1.23 mmol) were refluxed in THF (10 mL) under argon overnight. Cooled to room temperature, diluted with CH2Cl2 (20 mL) and water (5 mL) and the organic layer filtered through a phase separation tube and concentrated in vacuo. Dissolved in acetonitrile (5 mL) in a glass vial and methyl iodide (0.279 mL, 4.46 mmol) was added. The vial was capped and stood at room temperature for 24 h. The solvent was evaporated in vacuo and the residue triturated with heptane/EtOAc, 10/1 (10 mL) to give 3-(4-acetyl-piperazine-1-carbonyl)-1-methyl-3H-imidazol-3-ium iodide as a colourless gum (400 mg) which was used without further purification.

Workup

  1. filtrationthe organic layer filtered through a phase separation tube
  2. concentrationconcentrated in vacuo
  3. additionwas added
  4. customThe vial was capped
  5. customThe solvent was evaporated in vacuo
  6. customthe residue triturated with heptane/EtOAc, 10/1 (10 mL)

Sources & evidence

ORD record
ord-743bf43cbd7946598e4e3b5ffab1018e
Source dataset
uspto-grants-2014_02
Patent number
US08653092B2

Reaction notes

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