Morpholine → 4-Morpholinobenzaldehyde

HRID 1662995Notes

Reaction equation

HRID 1662995 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 2913494-Morpholinobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 15 g (120.86 mmol) of p-fluorobenzaldehyde in 200 ml of DMF, 16.8 g (193.4 mmol) of morpholine and 33.36 g (241.7 mmol) of potassium carbonate are added successively at r.t. After being stirred for 8 h at 100° C., the reaction mixture is cooled to r.t., diluted with ice water and then the mixture is extracted with AcOEt and CH2Cl2. The combined extracts are concentrated under reduced pressure and purified by silica gel column chromatography (eluent: n-Hexane:AcOEt=5:1˜3:1) to give 4-morpholin-4-yl-benzaldehyde. 1H-NMR (400 MHz, CDCl3): 3.35-3.40 (m, 4H), 3.85-3.90 (m, 4H), 6.92 (d, 2H, J=8.56 Hz), 7.77 (d, 2H, J=8.56 Hz), 9.80 (s, 1H).

Workup

  1. temperaturethe reaction mixture is cooled to r.t.
  2. extractionthe mixture is extracted with AcOEt and CH2Cl2
  3. concentrationThe combined extracts are concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (eluent: n-Hexane:AcOEt=5:1˜3:1)

Sources & evidence

ORD record
ord-6957ee8b0f1a42f0b9c4db82c9035141
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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