Pyridine → HCID 14576910, compound

HRID 1904628Notes

Reaction equation

HRID 1904628 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:22])=[CH:4][CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].N1C=CC=CC=1>C(Cl)(Cl)Cl.C(OC(C)C)(C)C>[C:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:22])=[CH:4][CH:3]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14576908HCID 14576908, compound

Product 1

HCID 14576910HCID 14576910, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 2.42 g of 1-(4-aminophenyl)-6-(3,4-dichlorophenyl)-2-piperidone in 20 ml of chloroform were added 5 ml of acetic anhydride and 0.5 ml of pyridine, and the mixture was stirred at room temperature for 30 minutes and then at 80° C. for 30 minutes. The reaction mixture was cooled and diluted with isopropyl ether. The crystals precipitated were filtered and recrystallized from a mixture of ethanol and dimethylformamide to give 2.69 g of 1-(4-acetylaminophenyl)-6-(3,4-dichlorophenyl)-2-piperidone as colorless prisms.

Workup

  1. waitat 80° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. customThe crystals precipitated
  4. filtrationwere filtered
  5. customrecrystallized from a mixture of ethanol and dimethylformamide

Sources & evidence

ORD record
ord-cc9515600eae422f8459ff4de110ae66
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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