Ethylene Glycol → N-(3-Methylphenyl)benzenemethanamine

HRID 1883363

반응식

HRID 1883363 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

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 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, Rƒ=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.

출처 및 근거

ORD 기록
ord-46b72ae4282347a0b1026dbb6f384aa2
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759554B2

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