1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinone → 4-Piperidinol, 4-(t-butyl)-1-((10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-, (+-)-

Participants

Reaction Steps

Solution of 5 parts of 1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinone in 150 parts by volume of benzene is added dropwise over a period of 50 minutes to a stirred, cooled solution of tert-butyllithium (33.8 parts by volume of 1.9 M ethyl ether solution) in 150 parts by volume of benzene under a nitrogen atmosphere. The resultant solution is stirred at ambient temperature for about 1 hour and quenched with the addition of 100 parts by volume of 10% ammonium chloride. The solution is stirred for additional 2 hours, the organic layer separated, washed with brine, dried with magnesium sulfate and concentrated in vacuo to give clear yellow oil. This oil is chromatographed on silica gel using 1% ethanol/methylene chloride as eluent to afford 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-methyl]-4-piperidinol melting at about 96°-98.5° C. This compound is represented by the following general formula ##STR27##

Provenance & Evidence