Potassium Carbonate → HCID 4780303, compound

HRID 272511Notes

Reaction equation

HRID 272511 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:11][CH:12]1[O:17][CH:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(OCC)(=O)C>[CH3:18][CH:16]1[O:17][CH:12]([CH3:11])[CH2:13][N:14]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1108622,6-DimethylmorpholineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 4780303HCID 4780303, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-nitropyridine (4.84 g, 23.84 mmol), tetra-n-butyl ammonium iodide (0.440 g, 1.19 mmol), 2,6-dimethyl-morpholine (3.02 g, 26.22 mmol) and potassium carbonate (3.62 g, 26.22 mmol) were mixed in DMSO (45 mL). The reaction mixture was warmed to 80° C. for 6 hours. The reaction mixture was diluted with ethyl acetate and filtered. The volume of the filtrate was reduced to remove ethyl acetate, and the remaining solution was diluted with water (50 mL). A precipitate immediately formed and was collected by filtration then washed on the funnel with water to provide 2,6-dimethyl-4-(6-nitro-pyridin-3-yl)-morpholine as an orange solid (4.39 g, 78.0%). 1H NMR 6 (400 MHz, CDCl3) 8.16 (d, J=9.0 Hz, 1H), 8.11 (d, J=2.9 Hz, 1H), 7.19 (dd, J=2.9, 9.3 Hz, 1H), 3.77 (m, 2H), 3.65 (dd, J=2.2, 12.9 Hz, 2H), 2.66 (dd, J=10.7, 12.5 Hz, 2H), 1.29 (d, J=6.4 Hz, 6H).

Workup

  1. filtrationfiltered
  2. customto remove ethyl acetate
  3. additionthe remaining solution was diluted with water (50 mL)
  4. customA precipitate immediately formed
  5. filtrationwas collected by filtration
  6. washthen washed on the funnel with water

Sources & evidence

ORD record
ord-f773f7a929184950bf5d35537b6cf807
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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