Ethylene Glycol → 6-Phenylhexan-1-amine

HRID 984610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984610
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].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([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH2:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

8

Edukt 4

HCID 174Ethylene GlycolHCID 8102HexylamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

Produkt 1

HCID 1455586-Phenylhexan-1-amineAusbeute 86 %

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 or air was followed using copper(I) iodide (10 mg, 0.05 mmol or 2.0 mg, 0.01 mmol), K3PO4 (425 mg, 2.00 mmol), hexylamine (159 μL, 1.20 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=0.5) afforded N-(phenyl)hexylamine (152 mg, 86% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Bomann, M. D.; Guch, I. C.; DiMare, M. J. Org. Chem. 1995, 60, 5995-5996.

Quellen und Nachweise

ORD-Eintrag
ord-976ba30bcf374ede9d0a350025195a6e
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867298B2

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