Morpholine → 1-(4-(Morpholinomethyl)phenyl)ethanone

HRID 2280961Notes

Reaction equation

HRID 2280961 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>O1CCCC1.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[N:12]1([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 5009465Benzaldehyde, 4-acetyl-

Product 1

HCID 581376931-(4-(Morpholinomethyl)phenyl)ethanone

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4.7 g of 1,4-dihydro-2,6-dimethyl-3,5-pyridinecarboxylate and 1.3 g of scandium triflate were added to 2.75 g of 4-acetylbenzaldehyde (18.56 mmol), 1.7 ml of morpholine and 3 g of 4 Å molecular sieves in 100 ml of tetrahydrofuran under argon, and the mixture was heated to reflux for 3 hours. The mixture was concentrated. The residue was mixed with ethyl acetate and washed with sat. NaHCO3 solution and sat. NaCl solution. Drying and evaporation of the mixture resulted in a crude product which was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 40-80%). 1.85 g of a yellowish oil were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe mixture was concentrated
  4. additionThe residue was mixed with ethyl acetate
  5. washwashed with sat. NaHCO3 solution and sat. NaCl solution
  6. customDrying
  7. customevaporation of the mixture
  8. customresulted in a crude product which
  9. customwas purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 40-80%)

Sources & evidence

ORD record
ord-019b893bcdeb41f7b2a8678a699dc4c8
Source dataset
uspto-grants-2015_09
Patent number
US09139557B2

Reaction notes

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