Hexamethylenediamine → Hexamethylenediammonium d-glucarate salt

Participants

Reaction Steps

Aqueous D-glucaric acid (1, ˜1 M, 5.00 mL) and aqueous hexamethylenediamine (1 M, 5.00 mL) were mixed in a round bottom flask, and stirred at room temperature for 10 min. The reaction mixture was then stirred at 75° C. for 4 h and concentrated to an amber syrup. Methanol (10 mL) was added drop-wise to the concentrated solution and the reaction mixture was stirred for 1 h. The top methanol phase was removed and the light amber syrup was washed with methanol (2×5 mL), and then dried under vacuum at room temperature for 24 h to give hexamethylenediammonium D-glucarate (4a)/1 and 6-[N-(6-ammoniumhexyl)]-D-glucaramates (4b and 4c) (1.36 g, 4.27 mmol, 85%).

Provenance & Evidence