4-(2-Fluoro-4-nitrobenzyl)morpholine → 3-Fluoro-4-morpholin-4-ylmethylphenylamine

HRID 56082Notes

Reaction equation

HRID 56082 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1>CO.[Pd]>[F:1][C:2]1[CH:14]=[C:13]([CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[NH2:15]

Participants

4

Reactant 1

HCID 219550274-(2-Fluoro-4-nitrobenzyl)morpholine

Product 1

HCID 219550133-Fluoro-4-morpholin-4-ylmethylphenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrobenzyl)morpholine (14.80 g, 62 mmol) in MeOH (100 mL) was added Pd/C (4.0 g). The reaction mixture was stirred at rt under H2 overnight and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a claybank solid (11.27 g, 87%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-0d576ea423314e0bb7f56e22029f8cce
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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