2-(4-(2,3-Epoxypropoxy)phenyl)acetamide → N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-2-methyl-1H-benzimidazole-1-propanamine

HRID 1388911Notes

Reaction equation

HRID 1388911 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][NH2:10])[C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[N:3]=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:10][CH2:9][CH2:8][CH2:7][N:6]2[C:5]3[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=3[N:3]=[C:2]2[CH3:1])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 1198572-(4-(2,3-Epoxypropoxy)phenyl)acetamideHCID 43794783-(2-methyl-1H-1,3-benzodiazol-1-yl)propan-1-amine

Product 1

HCID 13066757N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-2-methyl-1H-benzimidazole-1-propanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.16 grams of 2-methyl-1H-benzimidazole-1-propanamine and 4.56 grams of 1-[4-(2-amino-2-oxoethyl)phenoxy]-2,3-epoxypropane in 50 ml of 90% methanol was refluxed for 22 hours. The solvent was then evaporated to leave a thick oil which was 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 evaporated to leave a thick oily residue which solidified partially on standing. This was recrystallized from ethanol to give N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-2-methyl-1H-benzimidazole-1-propanamine melting at about 146°-149° C. This compound has the following structural formula: ##STR14##

Workup

  1. temperaturewas refluxed for 22 hours
  2. customThe solvent was then evaporated
  3. customto leave a thick oil which
  4. customwas chromatographed on a silica gel column
  5. additionThe fractions containing the desired product
  6. customThe solvent was evaporated
  7. customto leave a thick oily residue which
  8. customThis was recrystallized from ethanol

Sources & evidence

ORD record
ord-ab1383ff4e6146769f3b07620374bca0
Source dataset
uspto-grants-1984_02
Patent number
US04434174

Reaction notes

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