Morpholine → 4-(4,6-Dichloropyridin-2-yl)morpholine

HRID 1158614Notes

Reaction equation

HRID 1158614 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10](Cl)[N:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:14][C:12]1[CH:13]=[C:8]([Cl:7])[N:9]=[C:10]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:11]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 27665Pyridine, 2,4,6-trichloro-

Product 1

HCID 596738604-(4,6-Dichloropyridin-2-yl)morpholineYield 30.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Morpholine (5.0 g) was added to a suspension of 2,4,6-trichloropyridine (10.0 g) and sodium carbonate (5.9 g) in acetonitrile (100 mL). The reaction mixture was then stirred at 70° C. for 16 hours, cooled to ambient temperature, filtered through celite and concentrated in vacuo. The crude product was subjected to flash chromatography (SiO2, heptane/ethylacetate 4:1) to furnish 3.90 g (30% yield) of the title compound as an off-white solid. LC-MS (m/z) 323.8 (M+); tR=3.10, (UV, ELSD) 98.5%, 98.9%. 1H NMR (500 MHz, CDCl3): 3.50 (m, 4H), 3.80 (m, 4H), 6.45 (s, 1H), 6.67 (s, 1H).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad342e1018424028b5037a94ae8f959e
Source dataset
uspto-grants-2010_10
Patent number
US07812020B2

Reaction notes

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