Morpholine → 4-(4-Nitrophenyl)morpholine

HRID 1665656Notes

Reaction equation

HRID 1665656 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 252224-(4-Nitrophenyl)morpholineYield 66.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-fluoro-4-nitro-benzene (500 mg, 3.54 mmol), morpholine (620 mg, 7.08 mmol) and K2CO3 (733 mg, 5.3 mmol) in DMSO (5 mL) was irradiated in a microwave (160 W) for 30 seconds (3×10 seconds). The reaction mixture was cooled to room temperature and poured onto ice. The resulting precipitated was filtered to afford 490 mg (66%) of 4-(4-nitro-phenyl)-morpholine. 1H NMR: (DMSO-d6): δ 8.1 (m, 2H), 7.1 (m, 2H), 3.42 (t, 4H), 3.4 (t, 4H).

Workup

  1. customwas irradiated in a microwave (160 W) for 30 seconds (3×10 seconds)
  2. additionpoured onto ice
  3. customThe resulting precipitated
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-5cfae4c81232440283cc581fc32e7070
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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