4-(5-Fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl ester → 4-(2-Amino-5-fluoro-4-methyl-phenylamino)piperidine-1-carboxylic acid tert-butyl ester

HRID 1716606Notes

Reaction equation

HRID 1716606 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([CH3:22])=[CH:17][C:16]=2[N+:23]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([CH3:22])=[CH:17][C:16]=2[NH2:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 588522794-(5-Fluoro-4-methyl-2-nitro-phenylamino)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 588522874-(2-Amino-5-fluoro-4-methyl-phenylamino)piperidine-1-carboxylic acid tert-butyl esterYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(5-fluoro-4-methyl-2-nitro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (680 mg, 1.92 mmol) and 10% Pd/C (68 mg) in ethanol (20 mL) was shaken under hydrogen (50 psi) for 4 hours. The reaction mixture was filtered through a pad of Celite® and the volatiles were removed. The residue was purified by flash chromatography (10% CH3OH in CH2Cl2) to afford 4-(2-amino-5-fluoro-4-methyl-phenylamino)piperidine-1-carboxylic acid tert-butyl ester (500 mg, 80%) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. customthe volatiles were removed
  3. customThe residue was purified by flash chromatography (10% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-8b001d1b9c474ec5b48f504a76a585ae
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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