Synthesis
General procedure for the synthesis of 3-(4-pyridyl)propylamine from 2-(3-(pyridin-4-yl)propyl)isoindoline-1,3-dione:
Preparation of Example 2 4-(3-aminopropyl)pyridine (Intermediate 2-1): N-[3-(4-pyridinyl)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 3 hours. After completion of the reaction, the reaction mixture was allowed to stand, the insoluble material was filtered out and the filtrate was concentrated under reduced pressure. Chloroform (1 L) and 4 N aqueous sodium hydroxide (500 mL) were added to the residue, the layers were separated and the organic layer was dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure and subsequently purified by distillation under reduced pressure to give 20.5 g (60% yield) of 3-(4-pyridyl)propylamine as a colorless oil.IR (pure): 3362, 2933, 1603 cm^-1; Boiling point: 76.0-79.0 °C/40 Pa.
References
[1] Helvetica Chimica Acta, 1982, vol. 65, # 6, p. 1868 - 1884
[2] MedChemComm, 2014, vol. 5, # 1, p. 72 - 81
[3] Heterocycles, 2005, vol. 66, # 1, p. 161 - 166
[4] Patent: US2003/32623, 2003, A1
[5] Patent: WO2005/9941, 2005, A1. Location in patent: Page 30
