1-(2,2-Diphenylethyl)piperidin-4-one → 1-(2,2-Diphenylethyl)-4-methyl-4-piperidinol
Reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][Mg]Br>O1CCCC1>[CH3:22][C:12]1([OH:15])[CH2:13][CH2:14][N:9]([CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:11]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 0.28 parts of 1-(2,2-diphenylethyl)-4-piperidinone in 5 parts by volume of tetrahydrofuran under nitrogen atmosphere is added 2 parts by volume of 3 M solution of methylmagnesium bromide. The resultant mixture is stirred for about 2.5 hours and then quenched with the careful addition of 5 parts by volume of 10% ammonium chloride. The mixture is left standing overnight, partitioned between water and ethyl acetate, and the organic layer separated. The organic layer is then dried with brine and magnesium sulfate, and concentrated to give 4-methyl-1-(2,2-diphenylethyl)-4-piperidinol, as yellow solid. This compound is represented by the following structural formula ##STR40##