Toluene → 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-carbonyl]-4-piperidinol

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Reaction Steps

3 Parts of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carboxylic acid chloride and 1.75 part of 4-tert-butyl-4-piperidinol are admixed in 15 parts by volume of toluene and then 1.5 part of triethylamine is added. The resultant mixture is stirred, at 75° C. under a nitrogen atmosphere for about 1.5 hour and then 5 parts by volume of methylene chloride is added. The mixture is stirred for about 24 hours, and then concentrated on a rotary evaporator to give a tan solid. The solid is redissolved in chloroform, washed with 1 N hydrochloric acid twice, saturated sodium bicarbonate solution, and brine, dried with magnesium sulfate and concentrated in vacuo to give a yellow oil. The oil upon trituration with ethyl ether, affords 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)carbonyl]-4-piperidinol, as a white solid, melting at about 189°-190.5° C. after recrystallization from cyclohexane. This compound is represented by the following structural formula ##STR26##

Provenance & Evidence