Dichloromethane → (4-Nitrophenyl)methyl 3-oxo-1-piperazinecarboxylate

HRID 2216554Notes

Reaction equation

HRID 2216554 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][O:9][C:10](Cl)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClCCl.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:24].C(N(C(C)C)CC)(C)C>O1CCOCC1.O>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][O:9][C:10]([N:21]2[CH2:22][CH2:23][NH:18][C:19](=[O:24])[CH2:20]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 782054-Nitrobenzyl chloroformateHCID 81531DiisopropylethylamineHCID 231360Piperazin-2-one

Product 1

HCID 21941454(4-Nitrophenyl)methyl 3-oxo-1-piperazinecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

The 48.7% solution of p-nitrobenzyloxycarbonyl chloride in 1,4-Dioxane (10.7 mL) was added to the dichloromethane (110 mL) solution of piperazin-2-one (2.21 g) and diisopropylethylamine (4.6 mL) at 0° C. and stirred for 0.5 h at 0° C. Water (300 mL) was added to the reaction mixture, and extracted with dichloromethane (3×100 mL). The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduce pressure. The residue was applied to silica gel column chromatography, eluted with CHCl3-methanol (30:1), and the title compound was obtained as white solid (7.1 g, quant.).

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. washeluted with CHCl3-methanol (30:1)

Sources & evidence

ORD record
ord-54f4d991c81049efb6b1b85fa725dc5e
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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