Diisopropylamine → HCID 131721066, compound

Participants

Reaction Conditions

Reaction Steps

105 mg of allyl-methyl-[6-(3-methyl-benzo[d]isothiazol-6-yloxy)-hexyl]-amine (Ex. 2d) in 2 ml of THF are added dropwise over a period of 20 min. at -78° C. to a lithium diisopropylamide (LDA) solution previously prepared from 100 μl of diisopropylamine and 425 μl of n-butyllithium (1.6M in hexane) in 2 ml of THF. The mixture is stirred at -78° C., treated with 3,3-dimethylallyl bromide and thawed overnight. For the working-up, the mixture is again cooled to -78° C. and treated with 42 μl of acetic acid in 0.3 ml of ether. The mixture is added to ice-cold sodium hydrogen carbonate solution and the inorganic phase is extracted with methylene chloride. The organic phases are washed with sodium chloride solution and dried. The crude product obtained after concentration is purified by column chromatography (silica gel, CH2Cl2 :MeOH:NH4OH 95:5:0.5). 63 mg of allyl-methyl-[6-[3-(4-methyl-pent-3-enyl)-benzo[d]isothiazol-6-yloxyl-hexyl-amine are obtained. This is taken up in 2 ml of ethanol and treated with 18.1 mg of fumaric acid. After stirring the solvent is removed and the residue is lyophilized. There are obtained 80 mg of allyl-methyl-[6-[3-(4-methyl-pent-3-enyl)-benzo[d]isothiazol-6-yloxy]-hexyl-amine.fumarate (1:1), MS: m/e 357 (M+H+).

Provenance & Evidence