Dimethylformamide → HCID 68308566, compound

HRID 1021294Notes

Reaction equation

HRID 1021294 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.Br.Br[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.CN(C=O)C.[H-].[Na+]>C(Cl)(Cl)Cl.O>[O:1]=[C:2]1[N:7]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 127070373-(Bromomethyl)pyridine hydrobromide

Product 1

HCID 68308566HCID 68308566, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Benzyl 3-oxopiperazine-1-carboxylate (400 mg) and 3-(bromomethyl)pyridine hydrobromide (647 mg) were mixed with DMF (8 ml), and sodium hydride (55% suspended in oil) (194 mg) was added thereto at 0° C., followed by stirring at room temperature for 3 hours. Water and CHCl3 were added to the reaction mixture at 0° C., and the organic layer was washed with water and saturated brine, dried over anhydrous sodium carbonate, and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (EtOAc/hexane) to obtain benzyl 3-oxo-4-(pyridin-3-ylmethyl)piperazine-1-carboxylate (345 mg).

Workup

  1. additionwas added
  2. customat 0° C.
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium carbonate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-86645e6a6de846f3943ec8f77c8721ae
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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