2-(4-Methoxyphenyl)-1,1-dimethylethylamine → (r)-n-[2-Hydroxy-3-(3-chloro-2-cyanophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)-ethylamine hydrochloride

HRID 2302176

Reaktionsgleichung

Reaktionsgleichung von HRID 2302176
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[C:13]#[N:14])[C@@H:2]1[O:4][CH2:3]1.[CH3:15][C:16]([NH2:27])([CH3:26])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>>[ClH:12].[OH:4][C@@H:2]([CH2:1][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[C:13]#[N:14])[CH2:3][NH:27][C:16]([CH3:26])([CH3:15])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1

Komponenten

3

Edukt 2

HCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamineHCID 44186486(R)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile

Produkt 1

HCID 9867079(r)-n-[2-Hydroxy-3-(3-chloro-2-cyanophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)-ethylamine hydrochlorideAusbeute 80,2 %

Versuchsvorschrift

Using the method of Example 6, supra, (R)-3-chloro-2-cyanophenyl glycidyl ether (0.7 g, 3.34 mmol) and 1,1-dimethyl-(4-methoxyphenyl)ethylamine (0.72 g, 4.0 mmol) were used to prepare 570 mg of the title compound as a white solid: 1H-NMR (CDCl3) 9.65 (1H, br s), 8.2 (1H, br s), 7.4 (1H, t), 7.15 (2H, d), 7.03 (1H, d), 6.95 (1H, d), 6.8 (2H, d), 4.8 (1H, m), 4.3 (2H, d), 3.75 (3H, s), 3.4 (2H, m), 3.13 (2H, dd), 1.44 (3H, s), 1.40 (3H, s); 13C-NMR 161.9, 159.4, 138.2, 135.1, 132.4, 126.8, 122.8, 114.4, 114.2, 111.6, 104.0, 71.8, 66.0, 61.9, 55.8, 45.4, 43.9, 23.5, 23.3.

Quellen und Nachweise

ORD-Eintrag
ord-b22ff6aad165445da3e5319fdbfd526e
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06432656B1

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