Methyl iodide → Tert-butyl 4-methyl-3-oxopiperazine-1-carboxylate

HRID 1437226Notes

Reaction equation

HRID 1437226 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:17]I>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH3:17])[C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 18783916Tert-butyl 4-methyl-3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-oxopiperazine-1-carboxylic acid tert-butyl ester (0.303 g) in N,N-dimethylformamide (12 mL), sodium hydride (being washed with pentane and dried, 44.3 mg) was added at 0° C., followed by stirring for 10 minutes. To the reaction mixture, methyl iodide (0.141 mL) was added, and the resultant mixture was stirred at room temperature for 20 hours. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and washed with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, to thereby give the title compound as an oily product (0.308 g, 95%).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-18449280b1af4441b403f47516ed646c
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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