Potassium Hydroxide → HCID 59555412, compound

HRID 1668520Notes

Reaction equation

HRID 1668520 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[N:7]=1)(=O)C.[OH-].[K+]>C(O)C>[OH:4][CH2:5][C:6]1[N:7]=[C:8]([C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59555443HCID 59555443, compound

Product 1

HCID 59555412HCID 59555412, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1.13 g of 6-(morpholin-4-carbonyl)pyridin-2-ylmethyl acetate, 233 mg of potassium hydroxide and 1.5 mL of ethanol were added, and the mixture was heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was removed off in vacuo. The residue was purified by chromatography on silica gel (chloroform-methanol-triethylamine=500:25:1) to give 530 mg of (6-hydroxymethyl-pyridin-2-yl)morpholin-4-ylmethanone as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed off in vacuo
  9. customThe residue was purified by chromatography on silica gel (chloroform-methanol-triethylamine=500:25:1)

Sources & evidence

ORD record
ord-3d478bde3a3a4fed989bd94304f51027
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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