Benzoyl chloride → 10-(2-dimethylaminoethyl)-10,11-dihydro-5-phenylthiomethyl-5H-dibenzo[a,d]cyclohepten-5-benzoate

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Reaction Steps

A solution of phenylthiomethyllithium (~0.5 m) is prepared by reacting 6.22 g. (0.05 mole) of thioanisole in 72 ml. of dry tetrahydrofuran with 22.0 ml. of 2.3M solution of phenyllithium for 15 hours at room temperature under nitrogen. A solution of 1.94 g. (0.007 mole) of 10-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 40 ml. of tetrahydrofuran is then added to a 42 ml. (~0.021 mole) portion of the phenylthiomethyllithium with ice-cooling. Stirring is initiated at room temperature for 24 hours. The resulting 10-(2-dimethylaminoethyl)-10,11-dihydro-5-phenylthiomethyl-5H-dibenzo[a,d]cycloheptene-5-ol is then poured onto a saturated salt solution and extracted with ether and the ether solution dried over anhydrous magnesium sulfate. The ether solution is cooled in ice and treated with 4.5 ml. of n-butyllithium in hexane (1.54 M solution 0.007 ice and 0.96 ml. (0.008 mole) of benzoyl chloride in 10 ml. ether is then added. The mixture is stirred for 3 hours at room temperature, diluted with ether and washed with water, saturated with sodium bicarbonate and then washed again with water. The ether is dried over anhydrous magnesium sulfate, filtered and evaporated and the residue purified to give 10-(2-dimethylaminoethyl)-10,11-dihydro-5-phenylthiomethyl-5H-dibenzo[a,d]cyclohepten-5-benzoate.

Provenance & Evidence