Reaction #54346

Reaction equation

3-phenylpropylmagnesium bromide

1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone

tetrahydrofuran

ammonium chloride

tetrahydrofuran

→

title compound

1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol

Solvents

ether

Conditions

Workup

1. 1
   OtherTo a 0° C.
2. 2
   workup.ADDITIONis then added to 250 ml
3. 3
   DryingThe ether phase is dried over magnesium sulfate
4. 4
   Otherevaporated
5. 5
   OtherThe residue is purified via column chromatography on 200 g
6. 6
   Washof silica gel eluted with 50% ether-cyclohexane

Procedure

To a 0° C. solution of 7.0 mmols. of 3-phenylpropylmagnesium bromide in 7 ml. of tetrahydrofuran is slowly added a solution of 2.48 g. (5.0 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone in 10 ml. of tetrahydrofuran. The resultant mixture is stirred for one hour and is then added to 250 ml. of saturated ammonium chloride-250 ml. ether. The ether phase is dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 200 g. of silica gel eluted with 50% ether-cyclohexane to yield the title compound.

Source