Morpholine → 6-(Morpholin-4-yl)pyridin-2-amine

HRID 85192Notes

Reaction equation

HRID 85192 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CS(C)=O.O>[O:18]1[CH2:19][CH2:20][N:15]([C:6]2[N:5]=[C:4]([NH2:8])[CH:3]=[CH:2][CH:7]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 187718606-(Morpholin-4-yl)pyridin-2-amineYield 47.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture containing 4-chloro-2-aminopyridine (164; 26 g, 0.20 mol), K2CO3 (0.40 mol) and morpholine (48; 0.6 mol) in DMSO (150 mL) was stirred at 190° C. for 10 h. Upon cooling to room temperature, the reaction mixture was diluted with water (300 mL) and the resulting mixture was extracted with ethyl acetate (4×150 mL). The combined organic layers were washed with water (3×25 mL), dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1) to afford 6-morpholinopyridin-2-amine 165 (17 g, 47%) as a white solid.

Workup

  1. temperatureUpon cooling to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate (4×150 mL)
  3. washThe combined organic layers were washed with water (3×25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-f83e39c1864d4864ab68fe0d4718fa24
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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