Potassium Iodide → 1-[3,3-Bis(4-fluorophenyl)propyl]piperazine

HRID 2073482Notes

Reaction equation

HRID 2073482 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10]Br)=[CH:4][CH:3]=1.[N:19]1(C(OCC)=O)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH-].[K+]>C1(C)C=CC=CC=1.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 138832773-Bromo-1,1-bis(4-fluorophenyl)propane

Product 1

HCID 138832821-[3,3-Bis(4-fluorophenyl)propyl]piperazineYield 84.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

31.1 g (0.100 mol) of 3,3-bis(4-fluorophenyl)propyl bromide, 20.6 g (0.130 mol) of ethyl piperazine-1-carboxylate, 27.6 g (0.200 mol) of powdered potassium carbonate and 4.15 g of potassium iodide were heated at the reflux temperature in 400 ml of toluene for 31 hours; the precipitate was then filtered off and the filtrate was concentrated. The material thus obtained was dissolved in 450 ml of ethanol, 450 ml of 4N KOH were added and the mixture was heated under reflux for 9 hours. After customary working up (compare Example 3d), 26.8 g of product, melting point 58°-64° C., were obtained.

Workup

  1. filtrationthe precipitate was then filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe material thus obtained
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 9 hours

Sources & evidence

ORD record
ord-ca1feb9d1186454ab36772d0d5a42c07
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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