Triethylamine → 1-(4-Aminophenyl)piperidin-4-one

HRID 1900076Notes

Reaction equation

HRID 1900076 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.C(N(CC)CC)C>O1CCOCC1.[Pd]>[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 8471TriethylamineHCID 38425621-(4-Nitrophenyl)piperidin-4-one

Product 1

HCID 222202411-(4-Aminophenyl)piperidin-4-oneYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

5.6 g of 1-(4-nitrophenyl)-4-piperidone were suspended in 60 ml of dioxan under argon, treated with 2.6 ml of triethylamine and 0.6 g of palladium-on-charcoal (5%) and hydrogenated at room temperature and normal pressure. Filtration and concentration yielded 5.0 g of 1-(4-aminophenyl)-4-piperidinone.

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-081e7a810fdf4a13b85ad3f456a47a51
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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