2-Fluorobenzoyl chloride → HCID 24693692, compound

HRID 1529562Notes

Reaction equation

HRID 1529562 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[NH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1)=[O:5]

Participants

5

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 30848514-Piperidone hydrochloride

Product 1

HCID 24693692HCID 24693692, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluorobenzoyl chloride (10.5 g, 66.5 mmol) was added to a stirred solution of 4-piperidone hydrochloride (6.0 g, 60.5 mmol) and DIPEA (3.0 mL, 17.1 mmol) in DCM (150 mL). The mixture was stirred at room temperature for 2 hours and extracted with a 10% solution of citric acid, a saturated solution of Na2CO3 and H2O. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 1-(2-fluorobenzoyl)-4-piperidinone (5.5 g, 41% yield) that was used in the next step without further purification.

Workup

  1. extractionextracted with a 10% solution of citric acid
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-0792de5c38aa48ba8abb7b034dd43730
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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