Benzeneethanamine, 4-nitro-, hydrochloride (1:1) → HCID 178478810, compound

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Reaction Steps

4-(2-Guanidinoethyl)aniline dihydrochloride was prepared as follows. 4--Nitrophenethylamine hydrochloride (1.013 g, 5 mmol), 1H-pyrazole-1-carboxamidine hydrochloride (0.733 g, 5 mmol) and N-diisopropylethylamine (0.88 ml, 5 mmol) in acetonitrile (10 ml) and water (10 ml) were stirred at ambient temperature for 16 hours. Preparative RP-HPLC was carried out in two portions using a Dynamax 60A, C18 column (one inch internal diameter) eluting with acetonitrile and water containing 0.1% TFA to afford pure 4-nitrophenethylguanidine. The product was dissolved in water (10 ml) and one drop of concentrated hydrochloric acid was added, followed by 5% palladium on carbon (100 mg) and hydrogen was bubbled through the solution for 4 hours. The catalyst was removed by filtration and washed with water. Volatile material was removed by evaporation to give 4-(2-guanidinoethyl)aniline dihydrochloride as a brown foam (0.984 g) (after drying over potassium hydroxide pellets).

Provenance & Evidence