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-2ad94dae1a3a44fb8f5a2eb2c5b22950

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345064B2