Reaction #2045085

Reaction equation

2-(3-(5-Methyl-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione

→

3-(5-Methyl-1H-imidazol-1-yl)propan-1-amine

Solvents

EtOH

Conditions

Workup

1. 1
   Temperatureunder reflux over night
2. 2
   Concentrationmixture was concentrated down to a volume of 25 mL
3. 3
   workup.ADDITIONHydrochloric acid (conc., 55 mL) was then added
4. 4
   FiltrationThe formed precipitate was then filtered
5. 5
   TemperatureThe filtrate was cooled to 0° C.
6. 6
   workup.ADDITIONsolid NaOH was added until a final pH-value of 10-12
7. 7
   ExtractionThe aqueous solution was extracted by means of CHCl3 (3×50 mL)
8. 8
   DryingThe combined organic layers were dried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Otherthe solvent was removed
11. 11
    OtherThe product was purified by means of flash-chromatography

Procedure

2-(3-(5-Methyl-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione (i.e. 8.92 mmol, 1 eq., which may be prepared as described in D3) and hydzine monohydrate (17.84 mmol, 2 eq.) were dissolved in dry EtOH (50 mL). The mixture was kept under reflux over night, then 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.

Source