N,N'-Bis(1-methylethyl)urea → 1-(N-methyl,N-isopropylamino)-3,5-dimethyl-adamantane hydrochloride

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Reaction Steps

2.43 grams of 1-bromo-3,5-dimethyl-adamantane hydrochloride were heated in a closed vessel for 40 minutes at 180° C., with 2.8 grams of N,N'-di-isopropylurea. After cooling, the reaction product was suspended in 50 ml. of water, acidified, and extracted with two 10-ml. portions of ether. Next, the water phase was brought to a pH of between 12 and 13 with sodium hydroxide, stirred for 10 minutes, and extracted with four 10-ml. portions of benzene. The benzene extracts were combined, the benzene stripped off, and the residue refluxed for 10 hours with 4 ml. of a 32% formaldehyde solution and 4 ml. of concentrated formic acid. After cooling, the solution was worked up as in Example 6. It yielded 1.04 grams of 1-(N-methyl,N-isopropylamino)-3,5-dimethyl-adamantane hydrochloride. Yield: 38% of theoretical yield.

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