Piperidine-1-propylamine → HCID 44603110, compound

Participants

Reaction Steps

Under nitrogen atmosphere, 2-benzyl-3-oxoisoindoline-5-carboxylic acid (Chemical Formula 8) (100 mg, 0.374 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 0.144 g, 0.749 mmol), and 1-hydroxybenzotriazole (HOBT, 0.025 g, 0.187 mmol) were reacted at room temperature in distilled dichloromethane, with stirring, for 2 hours. After monitoring through TLC [CH2Cl2:MeOH=4:1], the temperature was decreased to −40° C. at which time 3-(piperidin-1-yl)propan-1-amine (80 μL, 0.562 mmol) was added before stirring for 3-4 hours. The reaction progress was monitored with TLC [Hex: EA=1:1]. When the reaction was completed, the reaction mixture was extracted with NaHCO3 and then with CH2Cl2. The organic layer thus obtained was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in a vacuum and the concentrate was purified using column chromatography [CH2Cl2:MeOH=20:1] to afford 2-benzyl-3-oxo-N-(3-(piperidin-1-yl)propyl)isoindoline-5-carboxamide (Chemical Formula 1) in an amount of 96 mg (Yield 73%). This product was solidified with ethereal HCl to give a hydrochloride.

Provenance & Evidence