Diethyl Ether → N'-(1-acetylpiperidin-4-ylidene)benzohydrazide

HRID 44646

Reaction equation

HRID 44646 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:11]([NH:19][NH2:20])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)C>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[N:20][NH:19][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11955BenzoylhydrazineHCID 122563N-Acetyl-4-piperidone

Product 1

HCID 57531701N'-(1-acetylpiperidin-4-ylidene)benzohydrazideYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 g (0.142 mol) of 1-acetyl-4-piperidone were dissolved in 400 mL of absolute ethanol and 21.2 g (0.156 mol) of benzoylhydrazine were added. The resulting solution was refluxed for 6 hours under stirring. The solvent was then removed in vacuo and the residue partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was triturated with diethylether and 30 g (83% yield) of the title compound were collected by filtration.

Workup

  1. temperatureThe resulting solution was refluxed for 6 hours
  2. customThe solvent was then removed in vacuo
  3. customthe residue partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d168168c723d46c08635a1699a165a5d
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Linked notes

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