2-(4-Methoxyphenyl)-1,1-dimethylethylamine → N-[2-Hydroxy-3-(2-chlorophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride

HRID 2415311Notes

Reaction equation

HRID 2415311 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])[CH:2]1[O:4][CH2:3]1.[CH3:13][C:14]([NH2:25])([CH3:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1>>[ClH:12].[OH:4][CH:2]([CH2:1][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])[CH2:3][NH:25][C:14]([CH3:24])([CH3:13])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamineHCID 1375002-(2-Chlorophenoxymethyl)oxirane

Product 1

HCID 22640862N-[2-Hydroxy-3-(2-chlorophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine HydrochlorideYield 139.4%

Procedure

Using the method of Example 25, supra, 2-chlorophenyl glycidyl ether (1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (1.25 mmol) yielded 279 mg of the title compound as a white solid: GC/EI-MS, m/z (rel. int.) 348 (M−15, 5), 245 (21), 244 (100), 242 (100), 163 (29), 121 (82), 114 (24), 77 (21), 71 (44), 70 (56), 58 (24).

Sources & evidence

ORD record
ord-60a7cc15830447aeae09185314df44f0
Source dataset
uspto-grants-2004_11
Patent number
US06818660B2

Reaction notes

Loading…