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

HRID 1664977Notes

Reaction equation

HRID 1664977 reaction equation
[C:1]([N:4]1[CH2:12][CH2:11][CH:7]([C:8](Cl)=[O:9])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl-:13].[Al+3].[Cl-].[Cl-].[CH:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[C:19](Cl)[CH:18]=1>>[Cl:13][C:20]1[CH:21]=[C:22]([Cl:23])[CH:17]=[CH:18][C:19]=1[C:8]([CH:7]1[CH2:11][CH2:12][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]1)=[O:9]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
90 °C

Procedure

Acetylisonipecotoyl chloride (8 g, 42 mmol) was solved in dichlorobenzene and aluminium chloride (11.2 gr, 894 mmol) was added portionwise. The mixture was refluxed at 90° C. for 4 h after complexion of the reaction. Ice/water was added to the mixture that was extracted with dichloromethane. After chromatography from heptane to EtOAc the product was obtained as a yellow oil (6.3 g, 50%). MS (m/e): 300.2 (M+H+)

Workup

  1. customafter complexion of the reaction
  2. extractionwas extracted with dichloromethane

Sources & evidence

ORD record
ord-2955cd39ed5549669260f60705d88513
Source dataset
uspto-grants-2011_10
Patent number
US08039490B2

Reaction notes

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