Ammonium Chloride → 10-(2-dimethylaminoethyl)-10,11-dihydro-5-trimethylsilylmethyl-5H-dibenzo[a,d]cyclohepten-5-ol

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Reaction Steps

A Grignard reagent is prepared by conventional techniques from 12.2 g. (0.1 mole) trimethylsilylmethyl chloride and 24.3 g. magnesium metal (0.1 atom) and 200 ml. ether. The resulting solution is treated with 27.9 g. (0.1 mole) of 10-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 100 ml. ether. Stirring is initiated and the mixture is heated at reflux for 5 hours, then cooled in ice and hydrolyzed with 150 ml. of saturated ammonium chloride. The layers are separated and the ether dried over anhydrous magnesium sulfate and evaporated to give 10-(2-dimethylaminoethyl)-10,11-dihydro-5-trimethylsilylmethyl-5H-dibenzo[a,d]cyclohepten-5-ol.

Provenance & Evidence