Iodoethane → HCID 10030569, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -4-(3,4,5-trimethoxybenzyl)piperazine-2-methanol (500 mg) obtained by the method in Working Example 19 and N,N-dimethylformamide (3 ml) is cooled to 0° C., to which is added, in limited amounts, 60% oily sodium hydride (80 mg). The reaction mixture is stirred for 30 minutes and then cooled to -20° C., followed by adding thereto dropwise a mixture of ethyl iodide (200 mg) and N,N-dimethylformamide (1 ml). After stirring for 4 hours at -20° C., the reaction mixture is poured into ice-water, followed by extraction with methylene chloride. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent:ethyl acetate-hexane-methanol=50:45:5) to give 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -2-ethoxymethyl-4-(3,4,5trimethoxybenzyl)piperazine as a colorless oily product (420 mg). This product is dissolved in ethyl acetate and converted to its hydrochloride with 4N HCl (ethyl acetate solution). To the mixture is added ethyl ether, and left standing to give the hydrochloride as colorless crystals, m.p. 169-171° C.

Provenance & Evidence