2,4-Difluorobenzoyl chloride → HCID 18623232, compound

HRID 324334Notes

Reaction equation

HRID 324334 reaction equation
Cl.[OH2:2].[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[F:10][C:11]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>C(Cl)Cl.C(N(CC)CC)C>[F:10][C:11]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:12]=1[C:13]([CH:6]1[CH2:7][CH2:8][NH:3][C:4](=[O:2])[CH2:5]1)=[O:14]

Participants

5

Reactant 2

HCID 5880812,4-Difluorobenzoyl chlorideHCID 2723901Piperonylamine

Product 1

HCID 18623232HCID 18623232, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 4-piperidinone monohydrate hydrochloride (2.00 g, 13.28 mmol) in CH2Cl2 (40 mL) and triethylamine (5.0 mL) was added 2,4-difluorobenzoyl chloride (2.84 g, 15.93 mmol). The resulting mixture was stirred at room temperature for 5 hours before quenching with aqueous NaHCO3 (30 mL). Extracted with EtOAc (3×50 mL), dried (MgSO4), and concentrated to a residue which was purified by flash chromatography (EtOAc:Hexanes 9:1 to 1:1 ) afford product as an oil (2.25 g, 71%).

Workup

  1. custombefore quenching with aqueous NaHCO3 (30 mL)
  2. extractionExtracted with EtOAc (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a residue which
  5. customwas purified by flash chromatography (EtOAc:Hexanes 9:1 to 1:1 )

Sources & evidence

ORD record
ord-086a9f26b9984120a6d40204a43dd6fa
Source dataset
uspto-grants-2001_04
Patent number
US06218390B1

Reaction notes

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