Nitrogen → 5-Pyrrolidinoamylamine

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 5-bromovaleronitrile (0.21 mL, 1.80 mmol), pyrrolidine (0.15 mL, 1.81 mmol), K2CO3 (498 mg, 3.60 mmol) and KI (60 mg, 0.36 mmol) in dry CH3CN (15 mL) was refluxed for 1 h. The mixture was filtered and concentrated under reduced pressure. A 0.05 mol/L solution of the crude nitrile (59 mg, 0.39 mmol) in EtOH (8 mL) was hydrogenated at rt using the H-Cube® (1 mL/min) with a Raney Nickel cartridge (30 mm) under 50 bar until completion of the reaction. The solution was then concentrated under reduced pressure to give crude 5-(pyrrolidin-1-yl)pentan-1-amine as a colorless oil. LC-MS-conditions 01: tR=0.16 min; [M+H]+=157.19.

Provenance & Evidence