Morpholine → 3-(2-Morpholino-2-oxoethoxy)benzaldehyde

HRID 1597882Notes

Reaction equation

HRID 1597882 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10])([OH:3])=O.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O1CCOCC1>[N:14]1([C:1]([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=[O:10])=[O:3])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 6018952-(3-Formylphenoxy)acetic acid

Product 1

HCID 164955713-(2-Morpholino-2-oxoethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(Carboxymethoxy)benzaldehyde (1.63 g, 9.05 mmol) was dissolved in p-dioxane (20 ml) and cooled in an ice bath and then N,N'-carbonyldiimidazole (1.9 g) was added in one portion. The reaction mixture was stirred for 30 minutes, then morpholine (0.8 ml) was added and the mixture was warmed to room temperature and stirred until the reaction was complete. The solvent was removed in vacuo, the residue was partitioned between CHCl3 (100 ml) and 2N HCl (75 ml), the layers were separated, and the aqueous layer was extracted with CHCl3 (2×75 ml). The organic layers were combined, dried over MgSO4 and stripped to afford an oil which was combined with the product from a similar experimental run and purified by column chromatography on silica gel eluting with chloroform to afford 2.1 g of 3-[4-morpholinylcarbonylmethoxy]benzaldehyde.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred until the reaction
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between CHCl3 (100 ml) and 2N HCl (75 ml)
  5. customthe layers were separated
  6. extractionthe aqueous layer was extracted with CHCl3 (2×75 ml)
  7. dry with materialdried over MgSO4
  8. customto afford an oil which
  9. custompurified by column chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-623b7ab41b60476d8f655aa9aea5a15c
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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