2-(4-(2,3-Epoxypropoxy)phenyl)acetamide → N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-alpha-methyl-1H-benzimidazole-1-propanamine
Reaction equation
[CH3:1][CH:2]([NH2:14])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.[NH2:15][C:16](=[O:29])[CH2:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][CH:24]2[O:26][CH2:25]2)=[CH:20][CH:19]=1>CO>[NH2:15][C:16](=[O:29])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH:24]([OH:26])[CH2:25][NH:14][CH:2]([CH3:1])[CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]=[CH:6]2)=[CH:27][CH:28]=1Participants
4
Procedure
A mixture of 1.65 grams of α-methyl-1H-benzimidazole-1-propanamine and 1.82 grams of 1-[4-(2-amino-2-oxoethyl)phenoxy]-2,3-epoxypropane in 6 ml. of 95 percent methanol was refluxed for 19 hours. The solvent was evaporated from the mixture and the residual solid was triturated several times with ether. The solid was then dried and chromatographed on a silica gel column using methanol. The fractions containing the desired product were determined by thin-layer chromatography and combined. The solvent was then evaporated to leave a residual oil which solidified on cooling to give N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-α-methyl-1H-benzimidazole-1-propanamine melting at about 139°-142° C. This compound has the following structural formula. ##STR18##