Morpholine → 4-{2-[2-Fluoro-5-(methyloxy)-4-nitrophenyl]ethyl}morpholine

HRID 419456Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[C:6]([F:11])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CC(O)C>[F:11][C:6]1[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH2:9][CH2:10][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 180 °C

Procedure

To 5-ethenyl-4-fluoro-2-nitrophenyl methyl ether (0.43 g, 2.2 mmol) in 10 mL of iPrOH was added, morpholine (0.56 g, 6.54 mmol). The mixture was heated to 180° C. 1.5 h in the microwave. The solvent was rotovaped down and the residue purified by flash chromatography to give the title compound of step A (0.4 g, 1.41 mmol, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 7.62 (d, J=8.80 Hz, 1H), 6.99 (d, J=6.23 Hz, 1H), 3.94 (s, 3H), 3.70-3.75 (m, 4H), 2.87 (t, J=7.33 Hz, 2H), 2.58-2.66 (m, 2H), 2.49-2.56 (m, 4H).

Workup

custom1.5 h
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-5c4483d6321447f38bf22e91c9a0c130
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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