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., 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).

1. temperatureunder reflux
2. temperatureunder reflux over night
3. concentrationthe mixture was concentrated down to a volume of 25 mL
4. additionHydrochloric acid (conc., 55 mL) was then added
5. waitkept at this temperature for 30 min
6. filtrationThe formed precipitate was then filtered
7. temperatureThe filtrate was cooled 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-d24d5d01e990443182ae3880c38a1d56

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08409837B2