1,4-Dioxane → 1-(4-Aminophenyl)piperidin-4-one

HRID 37847

Reaction equation

HRID 37847 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.O1CCOCC1>[Ni].CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][C:13](=[O:16])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 38425621-(4-Nitrophenyl)piperidin-4-one

Product 1

HCID 222202411-(4-Aminophenyl)piperidin-4-oneYield 55.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(4-nitro-phenyl)-piperidin-4-one (2.8 g, 12.7 mmol) in a mixture of 1:4 dioxane: methanol (100 mL) was hydrogenated over Raney nickel (1 g) under balloon pressure at ambient temperature overnight. The mixture was filtered through Celite and the filtrate was concentrated under vacuum. The resulting solid was washed with petroleum ether (2×10 mL) and dried to afford 1-(4-amino-phenyl)-piperidin-4-one (1.34 g, 55%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. washThe resulting solid was washed with petroleum ether (2×10 mL)
  4. customdried

Sources & evidence

ORD record
ord-9fd9cdc746864c5e85abe82bcbb9f9cc
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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