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

HRID 1500241Notes

Reaction equation

HRID 1500241 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CO>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 29054894-(2-Fluoro-4-nitrophenyl)morpholine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 ml 3-neck round bottom flask with mechanical stirrer, septum and drying tube was added 3,4-difluoronitrobenzene (1) (12.91 g, 81.1 mmol), methanol (60 ml) and morpholine (15.93 g, 16 ml, 183 mmol). The clear solution was heated at reflux with stirring for 2 hours. The reaction mixture containing yellow crystals was cooled in an ice bath for 1 hour with stirring. The crystals were collected by filtration and dried in vacuo (1 mm) at room temperature for 3 hours (16.99 g, 93%). Homogenous by TLC (silica gel, CHCl3) Rf=0.54 (yellow spot) 1H NMR (500 MHz, CDCl3) δ 8.00 (ddd, 1H, J=9 Hz, J=2.6 Hz, J=1 Hz), 7.92 (dd, 1H, J=13.1 Hz, J=2.5 Hz,), 6.92 (dd, 1H, J=8.8 Hz, J=8.8 Hz), 3.86 (dd, 4H, J=4.7 Hz, J=4.7 Hz), 3.28 (dd, 4H, J=4.7 Hz, J=4.7 Hz). LCMS (Method A) 0.79 min m/e 227.

Workup

  1. customIn a 250 ml 3-neck round bottom flask with mechanical stirrer, septum and drying tube
  2. temperatureThe clear solution was heated
  3. temperatureat reflux
  4. additionThe reaction mixture containing yellow crystals
  5. temperaturewas cooled in an ice bath for 1 hour
  6. stirringwith stirring
  7. filtrationThe crystals were collected by filtration
  8. customdried in vacuo (1 mm) at room temperature for 3 hours (16.99 g, 93%)
  9. customLCMS (Method A) 0.79 min m/e 227

Sources & evidence

ORD record
ord-8d14b9bd2dc54857a29c0500b4ef7db3
Source dataset
uspto-grants-2015_12
Patent number
US09206141B2

Reaction notes

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