Methylamine → HCID 13176824, compound

Participants

Reaction Conditions

Reaction Steps

Anhydrous glucose (36.00 g; Aldrich Chemical Company) is weighed into a glass liner. The glass liner is placed into a dry-ice bath and methyl amine gas (68.00 g; Matheson) is condensed into the glass liner. The liner is then loaded into a rocking autoclave (500 ml capacity). The autoclave is heated to 50° C. and rocked for 5 hours at 50° C. under 600 psig nitrogen to form the adduct (N-methylglucosylamine). The reaction is then cooled in a dry-ice bath. The autoclave is then vented cold. Raney nickel (7.2 g of a 50% suspension in water, W/2 type, Aldrich Chemical Company) is added. The reaction is heated to 50° C. under 500-600 psig hydrogen and is rocked for 16 hours. The reaction is cooled in dry-ice bath and vented and purged with nitrogen. The reaction solution is pressure filtered through a Zeofluor filter (PTFE, 47 mm, 0.5 micron filter) with a 4 inch bed of Celite 545 (Fisher Scientific Company). The filtrate is concentrated under a stream of nitrogen to give 8.9 g of white solid. The Celite plug is washed with about 300 mls of water and the water is stripped on a rotary evaporator to give 18.77 g of white solid. The two solids are combined as they are analyzed to be of similar composition (90+ purity by GC analysis). The product is N-methyl glucamine.

Provenance & Evidence