Dicyclohexylcarbodiimide → HCID 70051543, compound

Participants

Reaction Steps

Into a reaction vessel, were placed 1.00 g of 4-amino-5-chloro-2-methoxy benzoic acid, 0.75 g of 3-amino-1-ethyl-5-hydroxymethyl pyrrolidine, 0.83 g of 1-hydroxy-1H-benzotriazole monohydrate, 1.13 g of dicyclohexyl carbodiimide (DCC), 15 ml of tetrahydrofuran (THF) and 2 ml of dimethyl formamide (DMF), and thus obtained mixture was stirred at room temperature for 14 hours. Thereafter, the precipitated dicyclohexyl carbonyl urea (DCU) was removed off, the filtrate was concentrated under reduced pressure and the residue was added with a dilute hydrogen chloride solution and washed twice with chloroform. The aqueous solution was alkalized with sodium bicarbonate and then extracted twice with chloroform. The organic extract was washed with a saturated aqueous saline solution and dried over magnesium sulfate. The extract was concentrated under reduced pressure and the residue was added with toluene, from which crystalline material was precipitated and separated. This was treated in isopropyl alcohol with HCl gas to convert to its hydrochloride and the thus formed hydrochloride precipitate was separated to obtain 1.05 g of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-5-hydroxymethyl pyrrolidin-3-yl) benzamide hydrochloride (Compound of Example 1 in Table 1) M.p. 162° to 165° C.

Provenance & Evidence