Morpholine → HCID 59555451, compound

HRID 1172231Notes

Reaction equation

HRID 1172231 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=1)#[CH:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C(O)C>[N:11]1([CH2:2][CH2:1][C:3]2[N:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 56972612(6-Ethynylpyridin-2-yl)methanol

Product 1

HCID 59555451HCID 59555451, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(6-Ethynylpyridin-2-yl)methanol (320 mg) and morpholine (1 g) were dissolved in 3 mL of ethanol, and the solution was heated to reflux under argon atmosphere for 24 hours. After allowing the reaction to cool, the ethanol was removed under reduced pressure, and the residue was basified with aqueous sodium hydroxide, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by chromatography on silica gel (chloroform-methanol-aqueous ammonia=200:10:1) to give 122 mg of [6-(2-morpholin-4-ylethyl)pyridin-2-yl]methanol as a yellow oil.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux under argon atmosphere for 24 hours
  3. customthe reaction
  4. temperatureto cool
  5. customthe ethanol was removed under reduced pressure
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed
  10. customThe residue was purified by chromatography on silica gel (chloroform-methanol-aqueous ammonia=200:10:1)

Sources & evidence

ORD record
ord-7d1a4d5f75af4da093ad18ecc380f26e
Source dataset
uspto-grants-2010_11
Patent number
US07834002B2

Reaction notes

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