Benzene → HCID 3577020, compound

HRID 1443030Notes

Reaction equation

HRID 1443030 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.[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 4365031-Methylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3577020HCID 3577020, compoundYield 84%

Procedure

To a cooled suspension of anhydrous aluminum chloride (20 g, 75 mmol) in benzene 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 ethereal solution was dried over sodium sulfate and concentrated to give 9.5 g of the title compound in 84% 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 ethereal solution was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-df26932ea6a64c9bac6b4dd90fc94f74
Source dataset
uspto-grants-2010_02
Patent number
US07659395B2

Reaction notes

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