Hydrochloric Acid → (3R)-1-benzylpyrrolidin-3-amine

Participants

Reaction Steps

A solution of 30.6 g (0.1 mol) of [R]-2-[1-(phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione in 300 ml of methanol was treated with 6.4 g (0.2 mol) of hydrazine. The reaction was stirred at room temperature for 18 hours and treated with 12.5 ml (0.15 mol) of concentrated hydrochloric acid. The solid was removed by filtration; the precipitate was washed with ethanol and the filtrate evaporated in vacuo. The residue was dissolved in water, made basic with 20% sodium hydroxide saturated with sodium chloride and extracted with ether (3×250 ml). The combined ether layers were washed with saturated sodium chloride solution, dried (MgSO4), filtered and evaporated in vacuo. The residue was distilled in high vacuo to give 14.4 g of the title compound, bp 86°-87°/0.15 mm.

Provenance & Evidence