Hydrochloric Acid → HCID 10910573, compound

Participants

Reaction Steps

Gaseous hydrochloric acid was hubled for 5 minutes through a suspension of 4-(aminomethyl)benzoic acid (20 mmol) in 100 mL of methanol, upon which it dissolved. After heating at reflux for 10 minutes a precipitate was formed which was filtered off and washed with diethyl ether to yield 2.5 g (12.4 mmols, 62%) of 4-carbomethoxy-benzylammonium chloride. A solution of 1.5 g of this compound in 10 mL ethanolamine was heated at 37° C. overnight. After removal of the solvent by vacuum destillation, the residue was dissolved in 300 mL water and treated with 50 g of Dowex H+ (SO3H). The resin was washed several times with water and 50% aq. methanol. Treatment of the resin with 5% aq. ammonia and yielded 1.0 g (5.15 mmol, 69%) of amine 7 as a yellow solid, m.p. 140°-143° C. A sample (approx. 100 mg) was further purified by preparative reverse-phase HPLC to give the pure trifluoroacetate salt as a colorless solid after lyophilyzation, the latter was used as cofactor.

Provenance & Evidence