4-PYRIDINEPROPANAMINE

PREPARATION To a solution of 2-(3-(pyridin-4-yl)propyl)isoindoline-1, 3-dione (72; 10 g crude, assumed 36.5 mmol) in MeOH (50 mL) was added hydrazine hydrate (5.5 g, 110 mmol). The mixture was stirred at room temperature for 18 h, filtered and the filtrate was concentratedto an oil. The oil was triturated with chloroform, filtered, and the filtrate was concentrated to obtain 3-(pyridin-4-yl)propan-1-amine (Compound 73; 4.0 g, 80percent) which was used directly in the next step. MS (ESI) calcd for C8H12N2: 136.10.General procedure: 1, 1-thiocarbonyldiimidazole 82 (1.2 equiv) was dissolved in dry DMF at 50C. To this mixture, a solution of the appropriate amines 81a-j (1 equiv) and dry Et3N (1 equiv) in dry DMF was slowly added dropwise. The mixture was stirred at 50C, and the progress monitored by TLC or UPLC/MS. Then the reaction was cooled down, water was added, and the aqueous phase was extracted with EtOAc (3×10mL). Organic phases were washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash column chromatography was performed.PREPARATION 4-(3-Aminopropyl)pyridine (Intermediate No. 2-1) 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. IR(neat): 3362, 2933, 1603 cm-1 bp:76.0-79.0 C./40 PaAdd a solution of hydrazine (4.0 mL) in methanol (200 mL) to 2- (3-PYRIDIN-4-YL- propyl) ISOINDOLE-1, 3-dione (8. 0 G, 30 MMOL). AFTER 48 hours, filter the mixture and concentrate the filtrate, triturate with methylene chloride (150 mL), and filter a second time. Perform the filtrate via flash chromatography on silica gel eluting with 80: 18: 2 CHC13/MEOH/CONCENTRATED NH40H) to afford the title compound as a yellow oil (3.42 g, ). MS: m/e= 137 (MH+).To a solution of 2-(3-(pyridin-4-yl)propyl)isoindoline-1, 3-dione (72; 10 g crude, assumed 36.5 mmol) in MeOH (50 mL) was added hydrazine hydrate (5.5 g, 110 mmol). The mixture was stirred at room temperature for 18 h, filtered and the filtrate was concentratedto an oil. The oil was triturated with chloroform, filtered, and the filtrate was concentrated to obtain

Molecular Weight:136.19
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:136.100048391
Monoisotopic Mass:136.100048391
Topological Polar Surface Area:38.9
Heavy Atom Count:10
Complexity:77.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes