Morpholine → 4-(5-Bromo-3-nitropyridin-2-yl)morpholine

HRID 1431356Notes

Reaction equation

HRID 1431356 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 31455044-(5-Bromo-3-nitropyridin-2-yl)morpholine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a vial containing 5-bromo-2-chloro-3-nitropyridine (0.99 g, 4.16 mmol) in DMSO (4.0 mL) was added morpholine (0.8 mL, 9.19 mmol) dropwise. The reaction was stirred at 23° C. and monitored with TLC and LC-MS. After 20 h, LC-MS showed that the reaction was complete, then the mixture was diluted with water. After extracting three times with EtOAc, the organic layers were combined then washed with brine and dried over anhydrous magnesium sulfate. After filtration, the mixture was concentrated in vacuo to afford a yellow-orange solid as 4-(5-bromo-3-nitropyridin-2-yl)morpholine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.53 (1H, d, J=2.3 Hz), 8.47 (1H, d, J=2.3 Hz), 3.70 (4H, m), 3.41 (4H, m).

Workup

  1. extractionAfter extracting three times with EtOAc
  2. washthe organic layers were combined then washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a65dc280756f4eb889a103d37c574e94
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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