Ethylene Glycol → Piperazine, 1-methyl-4-phenyl-

HRID 984618Notes

Reaction equation

HRID 984618 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[C:17]1([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 11575IodobenzeneHCID 531671-MethylpiperazineHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 200991Piperazine, 1-methyl-4-phenyl-Yield 71%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), N-(methyl)piperazine (166 μL, 1.50 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rf=0.1) afforded N-phenyl-N′-(methyl)piperazine (125 mg, 71% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity.

Sources & evidence

ORD record
ord-e8359b70141e4fbf8af165140ed14a9c
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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