Piperazine → 4-Chlorobenzhydrol

HRID 497140

Reaction equation

HRID 497140 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.N1CCNCC1.C([O-])([O-])=[O:23].[K+].[K+]>CC(=O)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 2415844-Chlorobenzhydryl chloride

Product 1

HCID 84014-ChlorobenzhydrolYield 57%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-chloro-4-(chloro-phenyl-methyl)-benzene (4.12 g, 17.4 mmol) in butanone (20 ml), anhydrous piperazine (5.98 g, 69.6 mmol), anhydrous K2CO3 (2.40 g, 17.4 mmol) and KI (2.88 g, 17.4 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 (100 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 57% yield. D. Synthesis of 1-{4-[(4-Chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-3,3-diphenyl-propan-1-one

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 (100 ml)
  6. washwashed with water (30 ml)
  7. customDrying
  8. customremoval of the solvent

Sources & evidence

ORD record
ord-023affac69994085b27be9146dc4f795
Source dataset
uspto-grants-2005_09
Patent number
US06949554B2

Linked notes

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