Water → 4'-(2-Morpholinoethoxy)acetophenone

HRID 493378Notes

Reaction equation

HRID 493378 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18](F)=[CH:17][CH:16]=1)=[O:14].O>CN(C)C=O.C(OCC)(=O)C>[N:6]1([CH2:5][CH2:4][O:3][C:18]2[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH3:12])=[CH:16][CH:17]=2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 24758Sodium hydrideHCID 611632-Morpholinoethanol

Product 1

HCID 302564'-(2-Morpholinoethoxy)acetophenone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (3.18 g; 0.0795 mol of a powder dispersed at 60%) is added at 23° C. to a solution containing 4-(2-hydroxyethyl)morpholine (9.40 g, 0.072 mol) in dimethylformamide (60 ml). Stirring is maintained for 30 minutes then the compound 4-fluoroacetophenone (5 g, 0.0362 mol) is added. The reaction medium is stirred for one hour at 23° C. then cooled down to 0° C. and water is added. After the addition of ethyl acetate then extraction, the organic phase is washed with a saturated sodium chloride solution, dried over sodium sulphate then the solvent is evaporated off. The residue obtained is adsorbed on silica then purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 6-1). An orange-coloured oil is obtained.

Workup

  1. additionis added at 23° C. to a solution
  2. temperatureis maintained for 30 minutes
  3. stirringThe reaction medium is stirred for one hour at 23° C.
  4. extractionextraction
  5. washthe organic phase is washed with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customthe solvent is evaporated off
  8. customThe residue obtained
  9. customthen purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 6-1)
  10. customAn orange-coloured oil is obtained

Sources & evidence

ORD record
ord-b80efbc993d04e9fa4f26254d2ce8cc4
Source dataset
uspto-grants-2009_05
Patent number
US07534805B2

Reaction notes

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