((m-Tolyloxy)methyl)oxirane → 1-[[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-3-(3-methylphenoxy)-2-propanol

HRID 728819Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[N:13]1([C:18]2[CH:34]=[CH:33][C:21]([O:22][CH2:23][CH2:24][NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:20][CH:19]=2)[CH:17]=[CH:16][N:15]=[CH:14]1>CO>[N:13]1([C:18]2[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH2:24][N:25]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:11][CH:10]([OH:12])[CH2:9][O:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)=[CH:33][CH:34]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2.75 g (17 mmol) 2,3-epoxypropyl 3-methylphenyl ether in 50 mL methanol add 4.4 g (15 mmol) 2-[4-(1H-imidazol-1-yl)phenoxy]-N-(phenylmethyl)ethanamine and heat to 50° C. for 24 h. Follow the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol, 9:1). At the completion of the reaction, evaporate the solvents. The resulting oil is chromatographed on a silica gel column using 2% methanol in methylene chloride to provide the title compound.

Workup

customthe progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol, 9:1)
customAt the completion of the reaction
customevaporate the solvents
customThe resulting oil is chromatographed on a silica gel column

Sources & evidence

ORD record: ord-4a8f36ae9c944e81947a63aad64f64db
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051423

Reaction notes

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