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

HRID 2398289Notes

Reaction equation

HRID 2398289 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 was then allowed to stand overnight at room temperature 1-Acetyl-4-bromo-4-(p-fluorobenzoyl)piperidine hydrobromide precipitated and was collected by filtration and recrystallized from ethanol. Yield: 40.6 g., melting point 156°-159° C. In exactly the same manner, additional intermediates of this type are produced by substituting the selected starting materials from PREPARATION 2 in the procedure of PREPARATION 7.

Workup

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

Sources & evidence

ORD record
ord-15498e4ad86c4a8fbf2c71a3ff296bde
Source dataset
uspto-grants-1977_05
Patent number
US04024264

Reaction notes

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