4-Fluoro-1-(3-nitro-5-(trifluoromethyl)phenyl)piperidine → 3-(4-Fluoropiperidin-1-yl)-5-(trifluoromethyl)aniline

HRID 2200145Notes

Reaction equation

HRID 2200145 reaction equation
[F:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([N+:18]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[F:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:13]=2)[NH2:18])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 900206124-Fluoro-1-(3-nitro-5-(trifluoromethyl)phenyl)piperidine

Product 1

HCID 900326163-(4-Fluoropiperidin-1-yl)-5-(trifluoromethyl)anilineYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add Pd/C (10%, 70 mg) to the solution of 4-fluoro-1-(3-nitro-5-(trifluoromethyl)phenyl)piperidine (300 mg, 1.0 mmol) in methanol (10 mL), stir the mixture under hydrogen atmosphere for 16 hrs at room temperature. Filter and concentrate the filtrate to get the crude product (270 mg, 100%) which is used directly without further purification.

Workup

  1. filtrationFilter
  2. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-2f79a566dcc744149cf248499c1f9948
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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