Bromine → 1-[4-Bromo-4-(4-fluorobenzoyl)piperidin-1-yl]ethan-1-one

HRID 2397467Notes

Reaction equation

HRID 2397467 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:19]Br>C(Cl)(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([Br:19])([C:10](=[O:18])[C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidine

Product 1

HCID 214351141-[4-Bromo-4-(4-fluorobenzoyl)piperidin-1-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 36 g (0.145 mole) of 1-acetyl-4-(p-fluorobenzoyl)piperidine in 175 ml of chloroform was treated with fifteen ml of bromine. The mixture was heated at reflux for one hour and then allowed to stand overnight at room temperature. 1-Acetyl-4-bromo-4-(p-fluorobenzoyl)piperidine precipitated and was collected by filtration and recrystallized from ethanol. Yield 40.6 g, melting point 156°-159° C. In the same manner, additional intermediates of this type are produced by substituting the selected starting materials from Preparation 2 or 11 in the procedure of Preparation 4.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one hour
  3. custom1-Acetyl-4-bromo-4-(p-fluorobenzoyl)piperidine precipitated
  4. filtrationwas collected by filtration
  5. customrecrystallized from ethanol
  6. customIn the same manner, additional intermediates of this type are produced
  7. customfrom Preparation 2 or 11
  8. customin the procedure of Preparation 4

Sources & evidence

ORD record
ord-dda871476b584cdb9a48ed6028a64c2c
Source dataset
uspto-grants-1977_05
Patent number
US04021564

Reaction notes

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