4-(2,5-Dimethyl-4-nitrophenyl)-1-(4-methoxybenzyl)piperidin-2-one → 4-(4-Amino-2,5-dimethylphenyl)-1-(4-methoxybenzyl)piperidin-2-one

HRID 536371Notes

Reaction equation

HRID 536371 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:14](=[O:27])[CH2:13]1>CO.[Pd]>[NH2:8][C:6]1[C:5]([CH3:11])=[CH:4][C:3]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[C:14](=[O:27])[CH2:13]2)=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 1

HCID 671553414-(2,5-Dimethyl-4-nitrophenyl)-1-(4-methoxybenzyl)piperidin-2-one

Product 1

HCID 671555764-(4-Amino-2,5-dimethylphenyl)-1-(4-methoxybenzyl)piperidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4-(2,5-dimethyl-4-nitrophenyl)-1-(4-methoxybenzyl)piperidin-2-one (63 mg, 0.17 mmol) in MeOH (10 mL) was added 10% w/w Pd/C (6 mg), the mixture was degassed and stirred under H2 at room temperature for 14 hr. After removing the catalyst by filtration, the filtrate was concentrated to provide 4-(4-amino-2,5-dimethylphenyl)-1-(4-methoxybenzyl)piperidin-2-one as a pale yellowish oil. ESMS m/z 339.2 (M+H+).

Workup

  1. customthe mixture was degassed
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b7014f36c0a74805a66c3234b9f1cf35
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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