Morpholine → HCID 47126215, compound

HRID 1887712Notes

Reaction equation

HRID 1887712 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([NH:9][CH3:10])=[O:8].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:10][NH:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:3]=[CH:4][C:5]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 442030775-Fluoro-N-methyl-2-nitrobenzamide

Product 1

HCID 47126215HCID 47126215, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of 5-fluoro-N-methyl-2-nitrobenzamide (178 mg, 0.9 mmol) and morpholine (94 mg, 1.2 eq) in anhydrous DMF (3.0 mL) was added Cs2CO3 (350 mg, 1.2 eq). The mixture was stirred at 100° C. in an oil bath overnight. The mixture was cooled and the solvent was removed to obtain the crude which was purified by silica gel chromatography to obtain the desired compound N-methyl-5-morpholino-2-nitrobenzamide (206 mg, isolated yield 86%).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was removed
  3. customto obtain the crude which
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-2a2cc275958049249d5e8ba67384b62f
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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