1-Ethoxycarbonyl-4-(4-fluoro-2-nitroanilino)piperidine → 4-(2-Amino-4-fluoro-phenylamino)-piperidine-1-carboxylic acid ethyl ester

HRID 1870614Notes

Reaction equation

HRID 1870614 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[N+:20]([O-])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C1COCC1.C(O)C.[Pt]>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[NH2:20])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 137921621-Ethoxycarbonyl-4-(4-fluoro-2-nitroanilino)piperidine

Product 1

HCID 137921724-(2-Amino-4-fluoro-phenylamino)-piperidine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

This 1-ethoxycarbonyl-4-(4-fluoro-2-nitroanilino)piperidine (5.7 g, 18.3 mmol.) was dissolved in THF (50 mL) and diluted with ethanol (100 mL). After addition of 5% platinum/carbon catalyst (1.2 g), the hydrogenation of the nitro functional group was carried out at atmospheric pressure via a balloon over a four hour period. The catalyst was removed and the solvents evaporated to give 1-ethoxycarbonyl-4-(2-amino-4-fluoroanilino)-piperidine as a viscous oil which was used as is.

Workup

  1. customThe catalyst was removed
  2. customthe solvents evaporated

Sources & evidence

ORD record
ord-9183a7014d3848bc85fc967bbbeff005
Source dataset
uspto-grants-2000_08
Patent number
US06096763

Reaction notes

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