Morpholine → 4-(2-Fluoro-4-nitrobenzyl)morpholine

HRID 56081Notes

Reaction equation

HRID 56081 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[F:12].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.CCN(CC)CC>C(Cl)Cl>[F:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzene

Product 1

HCID 219550274-(2-Fluoro-4-nitrobenzyl)morpholineYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(bromomethyl)-2-fluoro-4-nitrobenzene (3.04 g, 13 mmol) in CH2Cl2 (50 mL) were added morpholine (1.74 g, 20 mmol) and Et3N (2.63 g, 26 mmol). The reaction was refluxed overnight, and then concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a yellow solid (2.05 g, 65%).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Sources & evidence

ORD record
ord-dfed6744368e48c6a83b967ab4f20742
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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