Ethylene Glycol → N-Methyl-N-phenylbenzylamine

HRID 984614

반응식

HRID 984614 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.C(O)CCC>[CH3:9][N:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 7669N-MethylbenzylamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

생성물 1

HCID 69191N-Methyl-N-phenylbenzylamine수율 74%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 2631-Butanol용매HCID 21226206Ethyl acetate hexane용매

실험 절차

The general procedure under argon was followed using copper(I) iodide (19 mg, 0.10 mmol), K3PO4 (425 mg, 2.00 mmol), N-methylbenzylamine (155 μL, 1.20 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 1-butanol (1.0 mL) at 90° C. Column chromatography using a solvent mixture (hexane/ethyl acetate=20/1, Rf=0.5) afforded N-methyl-N-phenylbenzylamine (146 mg, 74% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829-12842.

후처리

  1. customat 90° C

출처 및 근거

ORD 기록
ord-7684ca4f87274264a6600a8f2a999c66
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867298B2

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