Tetrahydrofuran → 3,5-Difluoro-4-(morpholin-4-yl)aniline

HRID 56298Notes

Reaction equation

HRID 56298 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C1COCC1>[Pd].C(O)C>[F:11][C:4]1[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[C:3]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[NH2:8]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 223856304-(2,6-Difluoro-4-nitrophenyl)morpholine

Product 1

HCID 218781683,5-Difluoro-4-(morpholin-4-yl)anilineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(2,6-difluoro-4-nitrophenyl)morpholine (4.71 g, 19.3 mmol), THF (30 mL), ethanol (30 mL) and Pd/C (2.0 g, 10%) was stirred at rt under H2 overnight. The mixture was filtered and concentrated in vacuo and the residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1) to give the title compound as a yellow solid (3.62 g, 88%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1)

Sources & evidence

ORD record
ord-426bb2edf27046da964079bf5092389d
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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