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)-, (+-)-
Reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][N:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:24]([Li])([CH3:27])([CH3:26])[CH3:25]>C1C=CC=CC=1>[C:24]([C:20]1([OH:23])[CH2:21][CH2:22][N:17]([CH2:16][CH:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=3)[CH2:18][CH2:19]1)([CH3:27])([CH3:26])[CH3:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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##