Morpholine → 2-Morpholinobenzaldehyde

HRID 594982Notes

Reaction equation

HRID 594982 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>>[O:13]1[CH2:14][CH2:15][N:10]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 27370102-MorpholinobenzaldehydeYield 63%

Conditions

Temperature
125 °C

Procedure

A mixture of 2-fluorobenzaldehyde (0.5 mL, 4.8 mmol), morpholine (0.6 mL, 1.5 eq) and potassium carbonate (1.3 g, 2 eq) was heated in the microwave at 125° C. for 2.5 h. After evaporation, the residue was partitioned between water and DCM, the aqueous phase extracted with DCM. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford 2-morpholinobenzaldehyde (0.57 g, 63%).

Workup

  1. customAfter evaporation
  2. customthe residue was partitioned between water and DCM
  3. extractionthe aqueous phase extracted with DCM
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbfbaecc44c24a90a12fd492781d33e0
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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