2-((1-Methylethoxy)methyl)oxirane → N-(2-Hydroxy-3-isopropoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine

HRID 1060352

Reaktionsgleichung

Reaktionsgleichung von HRID 1060352
[CH:1]([O:4][CH2:5][CH:6]1[O:8][CH2:7]1)([CH3:3])[CH3:2].[CH3:9][C:10]([NH2:21])([CH3:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>>[OH:8][CH:6]([CH2:5][O:4][CH:1]([CH3:2])[CH3:3])[CH2:7][NH:21][C:10]([CH3:20])([CH3:9])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1

Komponenten

3

Edukt 2

HCID 199202-((1-Methylethoxy)methyl)oxiraneHCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamine

Produkt 1

HCID 22640903N-(2-Hydroxy-3-isopropoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamineAusbeute 17,9 %

Versuchsvorschrift

Using the method of Example 15, supra, isopropylglycidyl ether (126 μL, 1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (197 mg, 1.1 mmol) were used to prepare 53 mg of the title compound as a clear, colorless oil; GC/EI-MS, m/z (rel. int.) 296 (M+1, 0.2), 280 (1.4), 222 (1.5), 174 (100), 132 (12), 121(24); 1H-NMR (CDCl3) 7.03 (2H, d, J=8.4), 6.77 (2H, d, J=8.4), 3.72 (3H, s), 3.70 (1H, m), 3.53 (1H, m), 3.38 (2H, m), 2.80 (1H, broad s), 2.73 (2H, m), 2.58 (4H, m) 1.09 (6H, m), 1.01 (3H, s), 0.99 (3H, s); 13C-NMR (CDCl3) δ 157.9, 131.2, 129.9, 113.2, 73.4, 71.2, 69.0, 54.9, 53.1, 46.2, 44.5, 31.5, 26.6, 26.4, 19.1, 13.8.

Quellen und Nachweise

ORD-Eintrag
ord-faaad640dab54dc4938c0a7b31f4f4a3
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521667B1

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