Morpholine → 4-(4-Nitro-2-(trifluoromethyl)phenyl)morpholine

HRID 56232Notes

Reaction equation

HRID 56232 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CCN(CC)CC>CCOC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 949542-Fluoro-5-nitrobenzotrifluoride

Product 1

HCID 6128564-(4-Nitro-2-(trifluoromethyl)phenyl)morpholineYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-fluoro-4-nitro-2-(trifluoromethyl)benzene (4.18 g, 20.0 mmol), morpholine (2.09 g, 24.0 mmol), Et3N (6.07 g, 60.0 mmol) and EtOAc (30 mL) was stirred at rt for 5 h. The mixture was then 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 yellow solid (5.0 g, 91%).

Workup

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

Sources & evidence

ORD record
ord-646dc45d94eb41b695772755f28c0efb
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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