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

HRID 646932

Reaction equation

HRID 646932 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.[CH3:18]C([O-])(C)C.[K+].CI>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:18])[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 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 586385404-Cbz-1-methyl-2-piperazinoneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-oxo-piperazine-1-carboxylic acid benzyl ester (2.00 g, 8.54 mmol) in DMF (30 mL) was added KOtBu (1.54 g, 13.7 mmol) under Ar. The resulting solution was stirred at room temperature for 15 min and cooled to 0° C. MeI (0.85 mL, 14 mmol) was then added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. DMF was removed in vacuo and the residue was chromatographed on silica (5-50% EtOAc:hexane) to obtain the title compound (1.40 g, 66%). 1H-NMR (CDCl3; 400 MHz): δ 7.32 (m, 5H), 5.13 (s, 2H), 4.13 (s, 2H), 3.70 (m, 2H), 3.34 (m, 2H), 2.97 (s, 3H)

Workup

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 h
  4. customDMF was removed in vacuo
  5. customthe residue was chromatographed on silica (5-50% EtOAc:hexane)

Sources & evidence

ORD record
ord-ebc6365f48494669a8f43f49246418fa
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Linked notes

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