Reaktion #2045086

Reaktionsgleichung

2-(3-(4-Methyl-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione

hydrazine monohydrate

→

3-(4-Methyl-1H-imidazol-1-yl)propan-1-amine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux
2. 2
   Temperaturunder reflux over night
3. 3
   Einengenthe mixture was concentrated down to a volume of 25 mL
4. 4
   workup.ADDITIONHydrochloric acid (conc., 55 mL) was then added
5. 5
   workup.WAITkept at this temperature for 30 min
6. 6
   FiltrationThe formed precipitate was then filtered
7. 7
   TemperaturThe filtrate was cooled to 0° C.
8. 8
   workup.ADDITIONsolid NaOH was added until a final pH-value of 10-12
9. 9
   ExtraktionThe aqueous solution was extracted by means of CHCl3 (3×50 mL)
10. 10
    TrocknenThe combined organic layers were dried over Na2SO4
11. 11
    Filtrationfiltered
12. 12
    Sonstigethe solvent was removed
13. 13
    SonstigeThe product was purified by means of flash-chromatography
14. 14
    workup.ADDITIONa CHCl3/MeOH-gradient containing aqueous ammonia (2% v/v)

Vorschrift

2-(3-(4-Methyl-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione (3.42 mmol, 1 eq., which may be prepared as described in D6) and hydrazine monohydrate (6.84 mmol, 2 eq.) were dissolved in 20 mL of ethanol and the mixture was stirred for 12 h under reflux. The mixture was kept under reflux over night, then the mixture was concentrated down to a volume of 25 mL. Hydrochloric acid (conc., 55 mL) was then added and the mixture was heated to 50° C. and kept at this temperature for 30 min. The formed precipitate was then filtered. The filtrate was cooled to 0° C. and solid NaOH was added until a final pH-value of 10-12 was reached. The aqueous solution was extracted by means of CHCl3 (3×50 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent was removed. The product was purified by means of flash-chromatography using silica gel and a CHCl3/MeOH-gradient containing aqueous ammonia (2% v/v).

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