Benzeneethanamine, 4-nitro-, hydrochloride (1:1) → HCID 178478810, compound
Reaction equation
[ClH:1].[N+:2]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].Cl.[N:15]1([C:20]([NH2:22])=[NH:21])[CH:19]=[CH:18][CH:17]=N1>C(#N)C.O>[ClH:1].[ClH:1].[NH:11]([CH2:10][CH2:9][C:8]1[CH:12]=[CH:13][C:5]([NH2:2])=[CH:6][CH:7]=1)[C:20]([NH2:21])=[NH:15].[N+:2]([C:5]1[CH:13]=[CH:12][C:17]([CH2:18][CH2:19][NH:15][C:20]([NH2:22])=[NH:21])=[CH:7][CH:6]=1)([O-:4])=[O:3]Participants
Procedure
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).
Workup
- washeluting with acetonitrile and water containing 0.1% TFA
Sources & evidence
- ORD record
- ord-6f61f3eafd974e86a713fcc5b4812298
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087336
Reaction notes
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