Sodium Hydroxide → N,N-dimethyl-N'-farnesylacetylethylenediamine

Participants

Reaction Steps

A solution of 12.3 g of N,N-dimethylethylenediamine in 50 cc of ether was placed in a three-necked flask equipped with a stirrer, a dropping funnel and a thermometer. Then 37 g of the above-mentioned farnesylacetyl chloride was added dropwise at 5° to 10° C. After completion of the dropping, the reaction was continued at room temperature for an hour. After the reaction, 70 g of a 10% aqueous solution of sodium hydroxide was added, the aqueous layer was separated from the ether layer and extracted with ether, and the ether extract was combined with the ether layer. The ether was distilled off from the ether solution. The residue was subjected to preparative liquid chromatography (Waters Associates, Prep LC/System 500), which gave 38.5 g of N,N-dimethyl-N'-farnesylacetylethylenediamine (1). The structure was identified by proton NMR and mass spectrometry (M.S.). The NMR data are shown below.

Provenance & Evidence