Methyl iodide → 4-Cbz-1-methyl-2-piperazinone

HRID 1436490Notes

Reaction equation

HRID 1436490 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:21]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:21])[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 586385404-Cbz-1-methyl-2-piperazinoneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 4-benzyloxycarbonylpiperazin-2-one (2 g, 8.6 mmol) in THF (10 mL). Add sodium hydride (236 mg, 9.4 mmol, 60% dispersion in mineral oil) in one portion and stir at room temperature for 30 min. Add iodomethane (0.8 mL, 13 mmol) and stir at room temperature overnight. Concentrate, add ethyl acetate and wash with water. Separate organic layer, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate) to give the title compound as a yellow oil (1.7 g, 82%).

Workup

  1. concentrationConcentrate
  2. additionadd ethyl acetate
  3. washwash with water
  4. washSeparate organic layer, wash with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-a3975763d88b46c092902f66e2dd8321
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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