Reaction #73775

Reaction equation

4-(4-Bromo-phenyl)-piperidin-4-ol

aluminium chloride

→

title compound

4-(4-Bromo-phenyl)-4-(4-chloro-phenyl)-piperidine

Solvents

chlorobenzene

chlorobenzene

Conditions

Workup

1. 1
   Otherquenched by addition of ice
2. 2
   workup.ADDITIONmethyl t-butyl ether added
3. 3
   workup.STIRRINGAfter stirring for 1 hour the precipitate
4. 4
   Filtrationwas collected by filtration
5. 5
   Washwashed with water, methyl t-butyl ether and water

Procedure

A suspension of 4-(4-Bromo-phenyl)-piperidin-4-ol (4.02 g, 15.7 mmol) in chlorobenzene (30 ml) was added dropwise to a suspension of aluminium chloride (7.32 g, 54.9 mmol) in chlorobenzene (10 ml) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours, quenched by addition of ice then methyl t-butyl ether added. After stirring for 1 hour the precipitate was collected by filtration washed with water, methyl t-butyl ether and water to afford the title compound (5.59 g, 92% yield). LC/MS: (PS-B3) Rt 3.57 [M+H]+ 350, 352.

Source