Triethylamine → HCID 86736570, compound

Participants

Reaction Steps

To a mixture of 17.9 g (0.05 mole) of the above trans-3,4-dichloro-N-[2-(N-allylamino)cyclopentyl]-aniline, released from its hydrochloride salt and 5.5 g (0.05 mole) of triethylamine in 400 ml of ethyl ether there was added dropwise 10.6 g (0.05 mole) of 2,2,2-trichloroethyl chloroformate in 50 ml of ethyl ether while cooling the reaction vessel in ice in 30 minutes. The mixture was then stirred overnight at room temperature. The next day 250 ml of saturated sodium bicarbonate solution was added. The organic layer was then separated and washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to a yellow oil, weighing 23.0 g. This was the crude sub-titled amine. A 1.0 g portion of this amine oil was converted to its hydrochloride salt with excess ethereal hydrogen chloride and the salt was recrystallized from a mixture of 15 ml of methanol and 80 ml of ethyl ether to obtain the trans-3,4-dichloro-N-[2-(N-allyl-N-trichloroethoxycarbonylamino)cyclopentyl]aniline hydrochloride, m.p. 160°-162° C., softens, then melts.

Provenance & Evidence