Morpholine → 4-(4-Morpholinobenzoyl)-nitrobenzene

HRID 723553Notes

Reaction equation

HRID 723553 reaction equation
F[C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[O:22]1[CH2:23][CH2:24][N:19]([C:2]2[CH:18]=[CH:17][C:5]([C:6]([C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)=[O:7])=[CH:4][CH:3]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 97658Methanone, (4-fluorophenyl)(4-nitrophenyl)-

Product 1

HCID 218770174-(4-Morpholinobenzoyl)-nitrobenzeneYield 91.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture containing 4-(4-fluorobenzoyl)-nitrobenzene (1.96 g, 8 mmol), morpholine (0.84 g, 9.6 mmol), and potassium carbonate (1.33 g, 9.6 mmol) in dimethyl sulfoxide (15 mL) was heated to 100–110° C. for 12 hours. The reaction mixture was cooled to room temperature and diluted with cold water, and filtered. The crude product was washed several times with water and dried to give 4-(4-morpholinobenzoyl)-nitrobenzene (2.28 g, 91%), m.p. 173–175° C., and was used in the next step without further purification.

Workup

  1. temperaturewas heated to 100–110° C. for 12 hours
  2. filtrationfiltered
  3. washThe crude product was washed several times with water
  4. customdried

Sources & evidence

ORD record
ord-23c925d9a77d4e7fb9023bfc35b98124
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

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