Ethylene Glycol → 6-Phenylhexan-1-amine

HRID 984610노트

반응식

HRID 984610 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 1455586-Phenylhexan-1-amine수율 86%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-976ba30bcf374ede9d0a350025195a6e
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867298B2

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