Hydrazine hydrate (1:1) → 3-(5-methyl-1H-imidazol-1-yl)propan-1-amine

Temperature

50 °C

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 hydrazine 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.

1. temperatureunder reflux over night
2. concentrationmixture was concentrated down to a volume of 25 mL
3. additionHydrochloric acid (conc., 55 mL) was then added
4. filtrationThe formed precipitate was then filtered
5. temperatureThe filtrate was cooled to 0° C.
6. additionsolid NaOH was added until a final pH-value of 10-12
7. extractionThe aqueous solution was extracted by means of CHCl3 (3×50 mL)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. filtrationfiltered
10. customthe solvent was removed
11. customThe product was purified by means of flash-chromatography

ORD record

ord-8b7600c43d264700b01def53a109e313

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859250B2