2-fluoro-4-nitro-N-(2-(piperidin-1-yl)ethyl)aniline → 2-fluoro-N1-(2-(piperidin-1-yl)ethyl)benzene-1,4-diamine

HRID 56188

Reaction equation

HRID 56188 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[NH:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1COCC1.[Pd]>[F:1][C:2]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:3]=1[NH:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 523235752-fluoro-4-nitro-N-(2-(piperidin-1-yl)ethyl)aniline

Product 1

HCID 549680042-fluoro-N1-(2-(piperidin-1-yl)ethyl)benzene-1,4-diamineYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-4-nitro-N-(2-(piperidin-1-yl)ethyl)aniline (1.87 g, 7.00 mmol) in THF (20 mL) was added catalyst Pd/C (0.50 g). The reaction mixture was stirred at rt under H2 overnight. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=15:1) to give the title compound as yellow oil (1.50 g, 90%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (V/V)=15:1)

Sources & evidence

ORD record
ord-50217416dbda4f2d806e4164644b02b6
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

Loading…