Hydrazine hydrate (1:1) → 3-(4-Methyl-1H-imidazol-1-yl)propan-1-amine

Temperature

50 °C

2-(3-(4-methyl-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione (3.42 mmol, 1 eq.) 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 mixture was concentrated down to a volume of 25 mL. After that hydrochloric acid (conc., 55 mL) was added and the mixture was heated up to 50° C. for and kept at this temperature for 30 min. The formed precipitate was filtered off. The filtrate was cooled down to 0° C. and solid NaOH was added until a final pH-value of 10-12 is 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).

1. temperatureunder reflux
2. temperatureunder reflux over night
3. concentrationmixture was concentrated down to a volume of 25 mL
4. additionAfter that hydrochloric acid (conc., 55 mL) was added
5. waitkept at this temperature for 30 min
6. filtrationThe formed precipitate was filtered off
7. temperatureThe filtrate was cooled down to 0° C.
8. additionsolid NaOH was added until a final pH-value of 10-12
9. extractionThe aqueous solution was extracted by means of CHCl3 (3×50 mL)
10. dry with materialThe combined organic layers were dried over Na2SO4
11. filtrationfiltered
12. customthe solvent was removed
13. customThe product was purified by means of flash-chromatography
14. additiona CHCl3/MeOH-gradient containing aqueous ammonia (2% v/v)

ORD record

ord-eaba5fab8638443b8a56235859f125c7

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034907B2