2-((4-Chlorophenoxy)methyl)oxirane → N-[2-Hydroxy-3-(4-chlorophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride

HRID 1060348Notes

Reaction equation

HRID 1060348 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[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][C:9]([Cl:12])=[CH:8][CH:7]=1)[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 915152-((4-Chlorophenoxy)methyl)oxiraneHCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamine

Product 1

HCID 18459608N-[2-Hydroxy-3-(4-chlorophenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine HydrochlorideYield 135.9%

Procedure

Using the method of Example 6, supra, 4-chlorophenyl glycidyl ether (185 mg, 1 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (269 mg, 1.5 mmol) were used to prepare 272 mg of the title compound as a white solid: GC/EI-MS, m/z (rel. int.) 348 (M-15, 1), 244 (35), 243 (15), 242 (100), 163 (9), 121 (24), 114 (7), 71 (24), 70 (26), 58 (15), 42 (7).

Sources & evidence

ORD record
ord-ad0db80498664c0291e43bafc5c176cc
Source dataset
uspto-grants-2003_02
Patent number
US06521667B1

Reaction notes

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