1-Benzyl-4-piperidone → HCID 68832454, compound

HRID 2111600Notes

Reaction equation

HRID 2111600 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([F:10])[CH:4]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH4+].[Cl-]>C1COCC1>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]([C:3]2[CH:8]=[CH:7][C:6]([F:9])=[C:5]([F:10])[CH:4]=2)([OH:24])[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 676754-Bromo-1,2-difluorobenzeneHCID 5462224Magnesium

Product 1

HCID 68832454HCID 68832454, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 7.55 g of magnesium in 50 ml of THF is added dropwise a solution of 50 g of 1-bromo-3,4-difluorobenzene in 100 ml of THF so as to reach and then maintain reflux, and the mixture is left at reflux for 2 hours with stirring. After cooling to rt, a solution of 49 g of 1-benzyl-4-piperidinone in 100 ml of THF is added dropwise and the mixture is then stirred at RT overnight. The reaction mixture is poured onto saturated NH4Cl solution and extracted with ether, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. 38.3 g of the expected product are obtained after crystallization from cyclohexane.

Workup

  1. temperaturemaintain
  2. temperaturereflux
  3. waitthe mixture is left
  4. temperatureat reflux for 2 hours
  5. stirringthe mixture is then stirred at RT overnight
  6. extractionextracted with ether
  7. dry with materialthe organic phase is dried over Na2SO4
  8. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-caa1e0ff25b94b6e91d5181de1b5b476
Source dataset
uspto-grants-2009_04
Patent number
US07521449B2

Reaction notes

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