Tert-butyl 4-(4-nitrophenyl)piperidine-1-carboxylate → tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

HRID 1242918Notes

Reaction equation

HRID 1242918 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 11392606Tert-butyl 4-(4-nitrophenyl)piperidine-1-carboxylate

Product 1

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

An ethanol solution (30 ml) of tert-butyl 4-(4-nitrophenyl)-1-piperidinecarboxylate (1.7 g) was subjected to catalytic hydrogenation using 10% palladium carbon (0.2 g) as a catalyst under normal temperature and normal pressure. After the catalyst was filtered off, the filtrate was concentrated to give tert-butyl 4-(4-aminophenyl)-1-piperidinecarboxylate as a viscous oily substance. The titled compound (2.2 g) was obtained as colorless crystals, by carrying out the same operation as in Example 1, using the resulting oily substance and 4′-chloro[1,1′-biphenyl]-4-carboxylic acid (1.43 g).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0a0be9c9a2f74025ad8403d67c93b6ae
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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