1-(aminomethyl)cyclopentanol hydrochloride

5117-85-1

76066-27-8

The general procedure for the synthesis of 1-(aminomethyl)cyclopentanol hydrochloride from 1-hydroxycyclopentanecarbonitrile was as follows: to a mixture of cyclopentanone (5.50 g, 65.0 mmol) and ZnBr2 (0.20 g, 8.00 mmol) under cooling in an ice bath, TMSCN (10.0 mL, 73.4 mmol) was slowly added, and the reaction was subsequently stirred at room temperature for mixture for 12 hours. The resulting cyanohydrin solution was slowly added dropwise to a suspension of LiAlH4 (8.34 g, 219 mmol) in THF (30.0 mL) at 0 °C, and the mixture was then heated to reflux for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and water (10.0 mL), 4M NaOH aqueous solution (10.0 mL), and water (10.0 mL) were added slowly and sequentially under vigorous stirring. Insoluble material was removed by filtration through a diatomaceous earth pad, and the organic phase was separated and dried with KOH. The dried organic phase was decanted, dried over Na2SO4, filtered and concentrated. The residue was dissolved in MTBE (100 mL), a dioxane solution (10.0 mL) of 4N HCl was added, and stirred at room temperature for 30 minutes. The resulting white solid precipitate was collected by filtration through a sintered funnel to afford the target product 1-(aminomethyl)cyclopentanol hydrochloride (6.68 g, 68% yield).