Methylhydrazine → 1-[(3-Chlorophenyl)methyl]-2,4-piperidinedione 4-(2-methylhydrazone)

HRID 1349517Notes

Reaction equation

HRID 1349517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][C:7]1=[O:13].[CH3:17][NH:18][NH2:19]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH2:11][CH2:10][C:9](=[N:19][NH:18][CH3:17])[CH2:8][C:7]1=[O:13]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 23077696HCID 23077696, compound

Product 1

HCID 690018381-[(3-Chlorophenyl)methyl]-2,4-piperidinedione 4-(2-methylhydrazone)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-Chlorobenzyl)piperidine-2,4-dione (1.2 g) was dissolved in ethanol (25 ml), and methylhydrazine (0.5 ml) was added. The mixture was heated under reflux for 1 hr. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:1) to give 1-(3-chlorobenzyl)-4-(methylhydrazono)piperidin-2-one (1.05 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:1)

Sources & evidence

ORD record
ord-c5871ef307b0401582e8fa351614e36d
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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