Morpholine → HCID 59555417, compound

HRID 1668519Notes

Reaction equation

HRID 1668519 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 702826-Methylpyridine-2-carboxylic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 59555417HCID 59555417, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methylpicolinic acid (1.37 g) and morpholine (870 mg) was dissolved in 30 mL of DMF, and thereto 1.6 g of HOBt was added under stirring at ice temperature. After the mixture was stirred at same temperature for 15 minutes, additionally 2.3 g of WSC was added, and the solution was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and water was added to the residue, and then the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The resulting residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine=900:30:1) to give 1.71 g of (6-methylpyridin-2-yl)morpholin-4-ylmethanone as a colorless oil.

Workup

  1. stirringAfter the mixture was stirred at same temperature for 15 minutes
  2. stirringthe solution was stirred at room temperature overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed
  9. customThe resulting residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine=900:30:1)

Sources & evidence

ORD record
ord-85ede04de14e4cc0a9b6404a56bd38a3
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

Loading…