Sodium Chloride → HCID 21453009, compound

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Reaction Steps

The intermediate N,N'-diethyl-trans-3-heptene-1,7-diamine was prepared in two steps as follows: To 100 ml. of pyridine cooled to 0° C. (in an ice-salt bath) was added dropwise with stirring 35.8 g. of acetic anhydride. To the cooled stirred solution was added 18 g. of trans-3-heptene-1,7-diamine in 40 ml. of pyridine at such a rate to keep the temperature less than 10° C.; the addition took about 45 minutes. The reaction mixture was stirred at 5°-10° C. for an additional 30 minutes, was next stirred at room temperature for 6 hours and then allowed to stand at 5° C. overnight. The clear solution was treated with 10 ml. of concentrated ammonium hydroxide with cooling and stirring. The solution was distilled under reduced pressure to remove most of the volatile materials to leave a clear viscous oil. The oil was treated with 100 ml. of water followed by the addition of solid sodium chloride. The mixture was extracted with five 50 ml. portions of chloroform. The combined chloroform extracts were shaken with 100 ml. of saturated brine containing 2 ml. of 6N hydrochloric acid and then dried over anhydrous potassium carbonate. The chloroform was distilled off in vacuo to yield a clear viscous oil which crystallized at room temperature. The solid was purified by dissolving it in chloroform-methanol, treating the solution with decolorizing charcoal and removing the solvents in vacuo to yield, as a clear colorless viscous oil which crystallized at room temperature to yield 28.3 g. of N,N'-(trans-3-heptene-1,7-diyl)bis(acetamide).

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