Methanol → n'-[(2-Chlorophenyl)(4-chlorophenyl)methyl]piperazine

HRID 2267958Notes

Reaction equation

HRID 2267958 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=O)C.CO.[OH-].[Na+]>O1CCCC1>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:12]([C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)[N:9]1[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18348169n-(Ethoxycarbonyl)-n'-[(2-chlorophenyl)(4-chlorophenyl)methyl]piperazine

Product 1

HCID 5181446n'-[(2-Chlorophenyl)(4-chlorophenyl)methyl]piperazineYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 0.9 gram (0.002 mole) of N-(ethoxycarbonyl)-N′-[(2-chlorophenyl)(4-chlorophenyl)methyl]piperazine in 10 mL of tetrahydrofuran was added 10 mL of methanol and 10 mL of aqueous 50% sodium hydroxide. Upon completion of the addition the reaction mixture was warmed to 80° C., where it stirred for 24 hours. At the end of this time the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in chloroform, and the solution was stirred for 40 minutes. The resulting precipitate was collected by filtration. The filtrate was concentrated under reduced pressure, yielding 0.6 gram of crude material. The crude material was purified by preparative thin layer chromatography (TLC). Elution was accomplished with 1:1 acetone: methanol. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.4 gram of N′-[(2-chlorophenyl)(4-chlorophenyl)-methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. concentrationAt the end of this time the reaction mixture was concentrated under reduced pressure
  3. dissolutionThe concentrate was dissolved in chloroform
  4. stirringthe solution was stirred for 40 minutes
  5. filtrationThe resulting precipitate was collected by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customyielding 0.6 gram of crude material
  8. customThe crude material was purified by preparative thin layer chromatography (TLC)
  9. washElution
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-270f6ef3eea445da80057d864bd3aff5
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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