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 1270639

Reaktionsgleichung

Reaktionsgleichung von HRID 1270639
[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-60fe56f58a824c2ebbfc9e4a2fc688f8
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202261B2

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