Water → 1-Methyl-2,6-diphenylpiperidin-4-one

HRID 77686

Reaktionsgleichung

Reaktionsgleichung von HRID 77686
[C:1]1([CH:7]=[CH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][NH2:20].O>CN(C)C=O>[C:1]1([CH:7]2[CH2:8][C:9](=[O:18])[CH2:10][CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:20]2[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 6329MethylamineHCID 95417Dibenzylidene acetone

Produkt 1

HCID 2807081-Methyl-2,6-diphenylpiperidin-4-oneAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1,5-Diphenyl-1,4-pentadien-3-one (20b, 4.00 g, 17.1 mmol) was dissolved in dimethyl formamide (60 ml). Methylamine (51, 6.0 ml, 70.0 mmol, 40% in water) was added and the mixture stirred for 96 hr at room temperature. The mixture was poured into water (250 ml) and stirred for 1 hr at room temperature. The resulting mixture was extracted into ethyl ether, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 2.74 g (60%) of a white solid: mp 147-149° C. [expected mp 148-150° C.]; 1H NMR δ 1.82 (s, 3H), 2.50, (dd, 2H, J=12.3, 2.5 Hz), 2.82 (t, 2H, J=13.3 Hz), 3.45 (dd, 2H, J=12.9, 2.4 Hz), 7.34, (m, 10H); 13C NMR: δ 40.8, 50.8, 70.2, 127.0, 127.6, 128.8, 143.1, 206.8.

Aufarbeitung

  1. stirringstirred for 1 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl ether
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8d5f91124d8d4b2d91d969bdc27243d3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

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