Morpholine → 1-[6-(Morpholin-4-yl)pyridin-3-yl]ethan-1-one

HRID 416229Notes

Reaction equation

HRID 416229 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>CCO>[N:11]1([C:2]2[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 106558851-[6-(Morpholin-4-yl)pyridin-3-yl]ethan-1-oneYield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 32 (1.25 g, 7.9 mmol) and morpholine (2.20 mL, 25.2 mmol) in EtOH (22 mL) was refluxed for 12 h and then evaporated to dryness. The residue was dissolved in EtOAc (200 mL), washed with saturated NaHCO3 (50 mL×2) and brine (50 mL), dried over Na2SO4, filtered and evaporated to afford the title compound 33a (1.66 g, quantitative yield) as a pale yellow solid.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in EtOAc (200 mL)
  3. washwashed with saturated NaHCO3 (50 mL×2) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7a51bdd3b1294f3386219cf986721fc0
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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