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 2415331Notes

Reaction equation

HRID 2415331 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 9867079(r)-n-[2-Hydroxy-3-(3-chloro-2-cyanophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)-ethylamine hydrochlorideYield 80.2%

Procedure

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.

Sources & evidence

ORD record
ord-b1b4bb8e2e8f49bf9a0b7347bdebe965
Source dataset
uspto-grants-2004_11
Patent number
US06818660B2

Reaction notes

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