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

HRID 44647Notes

Reaction equation

HRID 44647 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[N:10][NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(OCC)C>C(O)(=O)C.O=[Pt]=O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][NH:11][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 57531701N'-(1-acetylpiperidin-4-ylidene)benzohydrazide

Product 1

HCID 57531678N'-(1-acetylpiperidin-4-yl)benzohydrazideYield 92%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

30 g (0.12 mol) of N′-(1-acetylpiperidin-4-ylidene)benzohydrazide were dissolved in 500 mL of glacial acetic acid and 1 g of PtO2 were added. The mixture was hydrogenated at 40 psi for 12 hours at room temperature. The catalyst was then filtered on celite and the filtrate evaporated in vacuo. The residue was redissolved with dichloromethane and washed with aqueous NaHCO3. The solvent was dried over sodium sulfate and removed under reduced pressure to give, after trituration with diethylether, 28.6 g (92% yield) of the title compound.

Workup

  1. filtrationThe catalyst was then filtered on celite
  2. customthe filtrate evaporated in vacuo
  3. dissolutionThe residue was redissolved with dichloromethane
  4. washwashed with aqueous NaHCO3
  5. dry with materialThe solvent was dried over sodium sulfate
  6. customremoved under reduced pressure
  7. customto give

Sources & evidence

ORD record
ord-ad6be746df704342b4a985698538d415
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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