Tris(2-carboxyethyl)phosphine hydrochloride → 1,2,7-trimethyl-1H-benzimidazol-5-ylamine hydrochloride

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Reaction Steps

Under a nitrogen atmosphere, 200 mg (1.00 mmol) 5-azido-1,2,7-trimethyl-1H-benzimidazole, 420 mg (1.50 mmol) tris(2-carboxyethyl)phosphine-hydrochloride, 1.5 mL dioxane and 0.5 mL E-water were combined and the mixture was stirred at RT overnight. Then the reaction mixture was acidified and extracted with EtOAc. The aqueous phase was made alkaline with aqueous sodium hydroxide solution and extracted with DCM. The organic phase was dried on sodium sulphate, filtered and evaporated down. The residue was combined with ethereal hydrochloric acid and the hydrochloride that settled out as precipitate was suction filtered and dried.

Provenance & Evidence