Ethylenediamine → 2-[(3,4-dihydro-1-methyl-2-naphthalenyl)methyl]-4,5-dihydro-1H-imidazole

Participants

Reaction Conditions

Reaction Steps

To a mixture of 60 g (0.33 mole) of 3,4-dihydro-1-methyl-2-naphthaleneacetonitrile and 30 ml of ethylenediamine was added 3 ml of carbon disulfide. The reaction mixture was stirred under nitrogen and heated in an oil bath at 120° C. for 21 hours, and then cooled to room temperature and concentrated in vacuo to remove volatile substances. The solid material was collected, dissolved in 600 ml of chloroform and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was triturated with ether and dissolved in ethanol. The ethanol solution was acidified with ethanolic hydrogen chloride and ether was added until the solution became cloudy. The solid product which crystallized was collected and dried in vacuo to give 28.7 g of 2-[(3,4-dihydro-1-methyl-2-naphthalenyl)methyl]-4,5-dihydro-1H-imidazole in the form of its mono-hydrochloride salt, m.p. 223°-224° C. A recrystallization from the same solvent mixture gave a sample with m.p. 226°-229° C.

Provenance & Evidence