Chlorobenzene → 4-[p-Chlorobenzoyl]-1-methylpiperidine

HRID 1992703Notes

Reaction equation

HRID 1992703 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](Cl)=[O:13])[CH2:8][CH2:7]1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:12]([CH:9]2[CH2:10][CH2:11][N:6]([CH3:5])[CH2:7][CH2:8]2)=[O:13])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 4365031-Methylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2426804-[p-Chlorobenzoyl]-1-methylpiperidineYield 85%

Procedure

To a cold suspension of anhydrous aluminum chloride (20 g, 75 mmol) in chlorobenzene 30 ml at 0° C. was added 1-methylpiperidine-4-carboxylic acid chloride in small portions and the resulted mixture was refluxed for 3 hours. The reaction mixture was cooled down, poured into ice water. The organic phase was discarded. The aqueous solution was washed with 2×50 ml ethyl ether, basified with potassium hydroxide pellet slowly to pH>10 and extracted with ethyl ether 4×50 ml. The combined organic solution was dried over sodium sulfate and concentrated to give 11.2 g of desired product in 85% yield.

Workup

  1. temperaturethe resulted mixture was refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled down
  3. washThe aqueous solution was washed with 2×50 ml ethyl ether
  4. extractionextracted with ethyl ether 4×50 ml
  5. dry with materialThe combined organic solution was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b495b1647f6a414f85fd2c9769b78808
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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