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

HRID 2280961

Reaktionsgleichung

Reaktionsgleichung von HRID 2280961
[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

Komponenten

5

Edukt 2

HCID 8083MorpholineHCID 5009465Benzaldehyde, 4-acetyl-

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734571Scandium(III) triflateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-019b893bcdeb41f7b2a8678a699dc4c8
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139557B2

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