N,N-dimethyl-1-(4-nitrophenyl)piperidine-4-carboxamide → 1-(4-aminophenyl)-N,N-dimethylpiperidine-4-carboxamide

HRID 57575Notes

Reaction equation

HRID 57575 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]>CO.[Pd]>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][CH:5]([C:3]([N:2]([CH3:20])[CH3:1])=[O:4])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 16370119N,N-dimethyl-1-(4-nitrophenyl)piperidine-4-carboxamide

Product 1

HCID 393499181-(4-aminophenyl)-N,N-dimethylpiperidine-4-carboxamideYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N,N-dimethyl-1-(4-nitrophenyl)piperidine-4-carboxamide (2.5 g, 9.01 mmol) and 0.3 g of Pd/C in 20 mL of MeOH, under H2, was stirred at room temperature for 5 hours. The mixture was filtered, and the volatiles were removed in vacuo to give 1.9 g of 1-(4-aminophenyl)-N,N-dimethylpiperidine-4-carboxamide.

Workup

  1. filtrationThe mixture was filtered
  2. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-b7b469407947489d9cbf859dc3a5ce13
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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