1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 9924157, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Intermediate 25 (0.31 g) in dichloromethane (15 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.21 g) and O-tert-butyldimethylsilylhydroxylamine (0.17 g) and the mixture was stirred for 18 h, then washed with water (40 ml), and the aqueous extracted with dichloromethane (20 ml). The combined organic extracts were dried over magnesium sulphate (1 g) and evaporated to give a yellow gum. This was taken up in tetrahydrofuran (20 ml), cooled to 0° C. and tetrabutylammonium fluoride (1M, 1.08 ml) added and the reaction stirred for 8 min, before acetic acid (2 drops) was added. The solvent was removed in vacua, water (10 ml) was added, and the slurry extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with brine (30 ml), dried over magnesium sulphate (0.5 g) and the solvent removed in vacua. Purification by flash chromatography (silica, eluent 5% methanol/dichloromethane) yielded the title compound as a gummy solid (0.023g).

Provenance & Evidence