4-(4-Bromophenyl)-4-hydroxypiperidine → 4-(4-Bromophenyl)-4-(4-chlorophenyl)piperidine

HRID 1798346Notes

Reaction equation

HRID 1798346 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl-:15].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:2]3[CH:7]=[CH:6][C:5]([Cl:15])=[CH:4][CH:3]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 939114-(4-Bromophenyl)-4-hydroxypiperidineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 497607774-(4-Bromophenyl)-4-(4-chlorophenyl)piperidineYield 203.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
0 °C

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-33) Rt 3.57 [M+H]+350, 352.

Workup

  1. customquenched by addition of ice
  2. additionmethyl t-butyl ether added
  3. stirringAfter stirring for 1 hour the precipitate
  4. filtrationwas collected by filtration
  5. washwashed with water, methyl t-butyl ether and water

Sources & evidence

ORD record
ord-fd9ba94e315f48d592a55c7a32efb1c1
Source dataset
uspto-grants-2013_01
Patent number
US08343953B2

Reaction notes

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