Ethylene Glycol → N-BENZYLBENZENE-1,4-DIAMINE

HRID 1883370Notes

Reaction equation

HRID 1883370 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[CH2:9]([NH:16][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 108934-IodoanilineHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 4255417N-BENZYLBENZENE-1,4-DIAMINEYield 51%

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 (19 mg, 0.10 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (218 μL, 2.0 mmol), 4-iodoaniline (219 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL) at 90° C. Column chromatography using a solvent gradient (hexane/ethyl acetate=2/1 to 1/1, Rƒ=0.2) afforded 4-(N-benzyl)aminoaniline (101 mg, 51% isolated yield) as brown solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Araki, T.; Tsukube, H. J. Polym. Sci., Polym. Lett. Ed. 1979, 17, 501-505.

Workup

  1. customat 90° C

Sources & evidence

ORD record
ord-dd8ac3eb521b401c912d175b31c217d7
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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