Triethylamine → HCID 12862642, compound

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Reaction Steps

To a mixture of 3.03 g. (0.03 mole) of triethylamine and 9.96 g. (0.03 mole) of the free diamine, trans-3,4-dichloro-N-[2-(N-methylamino)cyclopentyl]aniline, released from its hydrochloride salt with sodium hydroxide, in 250 ml. of ethyl ether, there is added 6.36 g. (0.03 mole) of 2,2,2-trichloroethyl chloroformate in 50 ml. of ethyl ether. The mixture is stirred at room temperature for 2 hours. Then 100 ml. of saturated sodium bicarbonate solution is added. The organic layer is dried over magnesium sulfate and concentrated to a yellow oil. This oil is converted to its hydrochloride salt by treatment with excess ethereal hydrochloric acid. This salt is recrystallized from a mixture of 120 ml. of methanol and 400 ml. of ethyl ether. The subtitled salt weighs 11.25 g. (80% yield). The NMR, IR, UV and mass spectral data are consistent with the subtitled structure.

Provenance & Evidence