Morpholine → 4-(4-Methyl-3-nitrophenyl)morpholine

HRID 1366290Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 4-bromo-1-methyl-2-nitrobenzene (225 mg, 1.04 mmol), morpholine (125 μL, 1.25 mmol), and cesium carbonate (474.4 mg, 1.46 mmol) in toluene, palladium diacetate (31.2 mg, 0.139 mmol) and 2-(di-t-butylphosphino)biphenyl (125 mg, 0.403 mmol) are added and stirred at 100° C. for 5 hours. After cooling, the mixture is filtered to remove insoluble material. The filtrate is poured into water and extracted with ethyl acetate twice. The organic layer is washed with water and then brine, dried over magnesium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford 4-(4-methyl-3-nitrophenyl)-morpholine as a yellow solid.

Workup

additionare added
temperatureAfter cooling
filtrationthe mixture is filtered
customto remove insoluble material
additionThe filtrate is poured into water
extractionextracted with ethyl acetate twice
washThe organic layer is washed with water
dry with materialbrine, dried over magnesium sulfate
customevaporated in vacuo
customThe residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-94302755d11346169bcc1395d49429d9
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893074B2

Reaction notes

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