omega-Dialkylaminoalkyl ethers of 6-(benzyl or phenyl)-1,3,3-trimethyl-2-oxabicyclo [2.2.2]octan-6-ol with platelet antiaggregating and local anesthetic activities.
The synthesis of 1,3,3-trimethyl-6-phenyl-2-oxabicyclo[2.2.2]octan-6-ol 2 and 6-benzyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol 3 starting from (+)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one and phenylmagnesium bromide or benzylmagnesium chloride, respectively, is described. Alcohols 2 and 3 gave a series of omega-dialkylaminoalkyl ethers 4 by reaction as sodium salts with omega-chloroalkyldialkylamines in toluene solution. Some compounds 4, in particular those derived from alcohol 2, showed a strong platelet antiaggregating activity in vitro, superior to that of acetylsalicylic acid, as well as in general an appreciable local anesthetic activity and a weak sedative effect in mice.