A solution of 21.7 g (0.11 mole) 1-adamantanecarboxylic acid chloride in 100
ml ether was added to a solution of 19.4 g (0.22 mole) 2-
dimethylaminoethanol in 200 ml ether. The reaction mixture was stirred
overnight at room temperature. Then additional 15.0 g (0.17 mole) 2-
dimethylaminoethanol was added and the reaction mixture again stirred
overnight. The reaction mixture was poured into 300 ml water and treated
with 20 ml of 10% NaOH solution. From the ether layer was recovered 23.0 g
of 2-dimethylaminoethyl 1-adamantanecarboxylate as oil.
The 2-dimethylaminoethyl 1-adamantanecarboxylate was mixed with 1-
bromodecan and allowed to stand for about 6 weeks. The resultant crystalline
mass was washed with ether and dried to gave 2-(1’-
adamantanecarbonyloxy)ethyldimethyldecylammonium bromide as white
crystals, melting point 183°-184.5°C (two recrystallizations from ethyl
acetate).
