Carbamate → HCID 178465603, compound

Participants

Reaction Steps

To a 0° C. stirred solution of 1.0 g (4.62 mmol) of N-Boc-1,6-diaminohexane in 30 ml ethanol was added 0.86 g (4.62 mmol) of intermediate B. After two hours the solution was concentrated, diluted with water (50 ml), and extracted with ether twice. The aqueous phase was freeze-dried to yield 0.9 g of white sticky solid tert-butyl N-(6-((acetimidoyl) amino)hexyl)carbamate intermediate. A suspension of the carbamate above (0.88 g, 3 mmol) in 15 ml dioxane and 7.5 ml trifluoroactic acid was treated with 10 ml (40 mmol) of 4N hydrochloric acid in dioxane solution with stirring overnight. The mixture was diluted with ether (50 ml) and the solids were isolated by filtration to provide 0.7 g N-(6-aminohexyl)acetamidine as a white solid (66% yield from N-Boc-1,6-diaminohexane). M.P.=163°-164° C. Mass spectrum (CI) 158.1 (MH+, 100%).

Provenance & Evidence