Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

A solution of 2,6 -dimethyl-4 -heptanone (2.84 g, 20 mmol), ammonium acetate (15.4 g, 200 mmol) and sodium cyanoborohydride (0.93 g, 14 mmol) in methanol (75 mL) was stirred at room temperature for 20 hours. After cooling in an ice bath, the reaction mixture was acidified with concentrated HCl and concentrated under reduced pressure at 35° . The residue was partitioned between ethyl ether and water and the aqueous portion removed and made basic with 40% NaOH solution. Product was extracted into ethyl ether which was then washed with brine, dried (Na2SO4), filtered and concentrated to 1.22 g of product. Conversion to the HCl salt and recrystallation from MeOH-EtOAc gave 1.04 of pure HCl salt, mp 248°-50° dec.

Provenance & Evidence