Morpholine → 4-(3-Nitrophenyl)morpholine

HRID 912227Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N+:8]([C:4]1[CH:3]=[C:2]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a toluene solution (10 ml) of 1-bromo-3-nitro-benzene (303 mg), palladium acetate (9.0 mg), BINAP (37 mg) and cesium carbonate (978 mg), morpholine (209 μl) was added, degassed under ultrasonic irradiation. This was stirred at 100° C. for 6 hours, followed by addition of water (20 ml), which was extracted with ethyl acetate (20 ml×2), and the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (dichloromethane/methanol=100/1 to 20/1), to obtain the desired compound (236.7 mg, 57%).

Workup

customdegassed under ultrasonic irradiation
additionfollowed by addition of water (20 ml), which
extractionwas extracted with ethyl acetate (20 ml×2)
dry with materialthe organic layer was dried over sodium sulfate
filtrationAfter the sodium sulfate was filtered off
distillationthe solvent was distilled off under reduced pressure
customfollowed by purification by silica gel column chromatography (dichloromethane/methanol=100/1 to 20/1)

Sources & evidence

ORD record: ord-9d2a7bb95c54420ea73416df1b6424d8
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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