Piperazine → HCID 59716935, compound

HRID 1443045Notes

Reaction equation

HRID 1443045 reaction equation
Cl[CH:2]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH:2]([CH:3]2[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]2)[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 59716944HCID 59716944, compound

Product 1

HCID 59716935HCID 59716935, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-(chloro(4-fluorophenyl)methyl)-1-methylpiperidine (1.2 g, 4.12 mmol) in butanone (10 ml), anhydrous piperazine (1.43 g, 16.48 mmol), anhydrous K2CO3 (0.54 g, 4.14 mmol) and KI (0.65 g, 4.14 mmol) was refluxed under nitrogen for 18 hours. The mixture was then cooled and filtered and the solvent removed in vacuo. The residue was dissolved in CH2C12 (50 ml) and washed with water (30 ml). Drying and removal of the solvent followed by chromatography (CH2C12:CH3OH:NH4OH 90:10:0.5) afforded desired product in 62% yield.

Workup

  1. temperaturewas refluxed under nitrogen for 18 hours
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in CH2C12 (50 ml)
  6. washwashed with water (30 ml)
  7. customDrying
  8. customremoval of the solvent

Sources & evidence

ORD record
ord-4b745e3027184cef8b4befcb41317173
Source dataset
uspto-grants-2010_02
Patent number
US07659395B2

Reaction notes

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