Hydrazine hydrate (1:1) → 3-(Pyridin-4-yl)propan-1-amine

N-[3-(4-Pyridyl)propyl]phthalimide (67.1 g, 252 mmol) was mixed with methanol (504 ml) and hydrazine monohydrate (18.3 ml, 378 mmol), and the mixture was refluxed for three hours. The reaction mixture was allowed to stand, then an insoluble matter was filtered out, and the filtrate was concentrated under reduced pressure. Chloroform (1 liter) and a 4 N aqueous sodium hydroxide solution (500 ml) were added to the residue, layers were separated, and the organic layer was dried over sodium sulfate. The organic layer was concentrated under reduced pressure and then distilled under reduced pressure to give 20.5 g (60%) of the titled compound as a colorless oily matter.

1. temperaturethe mixture was refluxed for three hours
2. filtrationan insoluble matter was filtered out
3. concentrationthe filtrate was concentrated under reduced pressure
4. additionChloroform (1 liter) and a 4 N aqueous sodium hydroxide solution (500 ml) were added to the residue, layers
5. customwere separated
6. dry with materialthe organic layer was dried over sodium sulfate
7. concentrationThe organic layer was concentrated under reduced pressure
8. distillationdistilled under reduced pressure

ORD record

ord-32b25cabc2204a3c84c6a781a1d54418

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098226B2