Piperazine → 1-((4-Chlorophenyl)(1-methylpiperidin-4-yl)methyl)piperazine

HRID 1992706Notes

Reaction equation

HRID 1992706 reaction equation
Cl[CH:2]([C:10]1[CH:15]=[CH:14][C:13]([Cl: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>[Cl: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 597169334-(Chloro(4-chlorophenyl)methyl)-1-methylpiperidine

Product 1

HCID 597169371-((4-Chlorophenyl)(1-methylpiperidin-4-yl)methyl)piperazineYield 62%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-(chloro(4-chlorophenyl)methyl)-1-methylpiperidine (1.2 g, 4.66 mmol) in butanone (10 ml), anhydrous piperazine (1.58 g, 18.45 mmol), anhydrous K2CO3 (0.63 g, 4.61 mmol) and KI (0.76 g, 4.61 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 CH2Cl2 (50 ml) and washed with water (30 ml). Drying and removal of the solvent followed by chromatography (CH2Cl2: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 CH2Cl2 (50 ml)
  6. washwashed with water (30 ml)
  7. customDrying
  8. customremoval of the solvent

Sources & evidence

ORD record
ord-f074183e4eaa49f182a017430131d006
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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