1,4-Dichlorobenzene → 4-(2,4-dichlorobenzoyl)-N-acetylpiperidine

HRID 72850

Reaction equation

HRID 72850 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[CH:5]1[C:10](Cl)=[CH:9][CH:8]=[C:7]([Cl:12])[CH:6]=1.[C:13]([N:16]1[CH2:24][CH2:23][CH:19]([C:20](Cl)=[O:21])[CH2:18][CH2:17]1)(=[O:15])[CH3:14]>O>[Cl:1][C:9]1[CH:8]=[C:7]([Cl:12])[CH:6]=[CH:5][C:10]=1[C:20]([CH:19]1[CH2:18][CH2:17][N:16]([C:13](=[O:15])[CH3:14])[CH2:24][CH2:23]1)=[O:21]

Participants

5

Reactant 3

HCID 46851,4-DichlorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130763874-(2,4-dichlorobenzoyl)-N-acetylpiperidineYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aluminium chloride (11, 24 g, 84 mmol) is added portionwise to 23 mL of dichlorobenzene (200 mmol). To this suspension 8 g of 1-acetylisonipecotoyl chloride (42 mmol) was added also portionwise. The mixture was stirred 10 minutes at room temperature and then at 90° C. for 4 hours until TLC indicated completion of the reaction that changed from a yellow/orange solution changed into dark orange upon heating. Water was added and the solution was extracted three times with dichloromethane. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash-chromatography on silica gel with hexane:ethyl acetate (1:0 to 0:1) to give 6.3 g (50%) of the product as an orange oil. MS (m/e): 300.2 (M+).

Workup

  1. waitat 90° C. for 4 hours until TLC indicated
  2. customcompletion of the reaction
  3. temperatureupon heating
  4. extractionthe solution was extracted three times with dichloromethane
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash-chromatography on silica gel with hexane:ethyl acetate (1:0 to 0:1)

Sources & evidence

ORD record
ord-d08775b157c249249f66914995cf0109
Source dataset
uspto-grants-2014_09
Patent number
US08829029B2

Linked notes

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