Diethylamine → 2,6-Octadien-1-amine, N,N-diethyl-3,7-dimethyl-, (2E)-

Participants

Reaction Conditions

Reaction Steps

Dry diethylamine (84 ml, 0.816 mole) was charged into a 500 ml 3 necked flask equipped with reflux condenser, thermometer, addition funnel and magnetic stirrer. The flask was swept out with dry nitrogen and maintained under a nitrogen blanket. Butyl lithium (16.6 ml, 2.2 M) in hexane was then added and the temperature raised to 50° C. After 15 minutes 200 ml 85% myrcene (1 mole) was added. The mixture exothermed and was cooled to 60°. After 4 hours at 60°, gas chromatography indicated that the amine had been converted to virtually a single product in high yield. Distillation gave a fraction boiling at 108° C./7 mm which was identified as diethylgeranylamine. The yield was 148.7 g (87% based on the amine used) of a product which was 96% "geranyl amine". (See Table I).

Provenance & Evidence