Ethylene Glycol → N-(3-Methylphenyl)benzenemethanamine

HRID 1243012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243012
[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:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[C:20]1([CH3:24])[CH:21]=[CH:22][CH:23]=[C:18]([NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:19]=1

Komponenten

8

Edukt 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 122683-IodotolueneHCID 62657Potassium Phosphate, Tribasic

Produkt 1

HCID 222281N-(3-Methylphenyl)benzenemethanamineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 3-iodotoluene (128 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=0.5) afforded N-(3-tolyl)benzylamine (171 mg, 87% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Spagnolo, P.; Zanirato, P. Tetrahedron Lett. 1987, 28, 961–964.

Quellen und Nachweise

ORD-Eintrag
ord-a1a8e9f3746d4140b37dcfbf92cb081d
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115784B2

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