Reaktion #1861448

Reaktionsgleichung

N-cinnamyl phthalimide

hydrazine hydrate

→

cinnamyl amine

Ausbeute 30.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the solvent was removed by a rotary evaporator
2. 2
   workup.ADDITIONthe solid residue was treated with 1 N NaOH (30 mL)
3. 3
   Extraktionthe resulting mixture was extracted with EtOAc (4×50 mL)
4. 4
   Sonstigedried
5. 5
   SonstigeEvaporation of the solvent under reduced pressure
6. 6
   Sonstigeafforded the crude product, which
7. 7
   Sonstigewas purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM)

Vorschrift

N-cinnamyl phthalimide (3 mmol) was mixed with 65% hydrazine hydrate (6 mmol, 2 equiv) and MeOH (10 mL), and the mixture was heated at 70° C. for 2 h. After the solvent was removed by a rotary evaporator, the solid residue was treated with 1 N NaOH (30 mL), and the resulting mixture was extracted with EtOAc (4×50 mL) and dried. Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 5-20% MeOH in DCM) to give cinnamyl amine. Compound 117 (white solid) was obtained at 30% yield, and compound 119 (off-white solid) was obtained at 80% yield. Identity was confirmed by 1H NMR (400 MHz, CD3OD).

Quelle