Reaktion #164868

Reaktionsgleichung

1,5-Diphenyl-1,4-pentadien-3-one

Methylamine

water

→

white solid

Ausbeute 60.4%

2,6-Diphenyl-1-methyl-4-piperidone

Ausbeute 60.4%

Lösungsmittel

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 1 hr at room temperature
2. 2
   ExtraktionThe resulting mixture was extracted into ethyl ether
3. 3
   Waschenwashed with saturated sodium chloride
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto afford a solid
8. 8
   SonstigeThe crude solid was recrystallized from ethanol

Vorschrift

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.

Quelle