Allyl iodide → Benzyl 3-oxo-4-(prop-2-en-1-yl)piperazine-1-carboxylate

HRID 1436508Notes

Reaction equation

HRID 1436508 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+].[CH2:20](I)[CH:21]=[CH2:22]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:22][CH:21]=[CH2:20])[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 11166Allyl iodideHCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 22894661Benzyl 3-oxo-4-(prop-2-en-1-yl)piperazine-1-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add to a solution of 4-benzyloxycarbonylpiperazin-2-one (1.6 g, 6.8 mmol) in dry THF (10 mL/mmol) under nitrogen, sodium hydride (188 mg, 7.4 mmol, 60% dispersion in mineral oil) in one portion and stir at room temperature for 30 min. Add allyl iodide (0.9 mL, 10 mmol) and stir at room temperature overnight. Concentrate, add ethyl acetate and wash with water, saturated aqueous sodium chloride solution, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:1 hexanes/ethyl acetate) to give the title compound as an oil (1.3 g, 72%).

Workup

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

Sources & evidence

ORD record
ord-65670dcda9e9408393b670e2ec313704
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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