Hydrochloric Acid → HCID 19969626, compound

Participants

Reaction Steps

The ketone (10.72 g, 0.05 mol) prepared in step (a) above was combined with ammonium acetate (38.73 g, 0.5 mol), sodium cyanoborohydride (2.22 g, 0.035 mol) and absolute methanol (200 ml) and stirred at room temperature for 3 days. The mixture was acidified to pH 1 with concentrated HCl, then the methanol was evaporated. The residue was partitioned between water and chloroform and the aqueous layer was separated and basified with solid KOH. The precipitate was extracted into chloroform and the chloroform layer was dried (MgSO4). Concentration of the solvent afforded the amine as a syrup (3.3 g). The amine was converted to the hydrochloride by dissolving in ethyl acetate and adding a saturated solution of hydrogen chloride in isopropanol until acidic. The precipitated solid was filtered and recrystallized from ethanol/ether to give the title compound as a white solid (2.54 g), mp 202°-207° C. (dec).

Provenance & Evidence