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

HRID 1902454Notes

Reaction equation

HRID 1902454 reaction equation
[N:1]1([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]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][CH2:13][CH2:12][CH2:11][CH2:10][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 1198572-(4-(2,3-Epoxypropoxy)phenyl)acetamideHCID 43794811H-Benzimidazole-1-butanamine

Product 1

HCID 13066754N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-butanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.84 grams of 1H-benzimidazole-1-butanamine and 3.11 grams of 1-[4-(2-amino-2-oxoethyl)phenoxy]-2,3-epoxypropane in 50 ml of 90% methanol was heated at reflux for 22 hours. The solvent was evaporated and the residue was triturated with ether to give an off-white solid. This 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 then evaporated to give N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-butanamine as an off-white solid melting at about 119°-123° C. This compound has the following structural formula: ##STR13##

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 hours
  3. customThe solvent was evaporated
  4. customthe residue was triturated with ether
  5. customto give an off-white solid
  6. customThis was chromatographed on a silica gel column
  7. additionThe fractions containing the desired product
  8. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-2bee466f57a54b5e8c5f8f9364bfbb22
Source dataset
uspto-grants-1982_12
Patent number
US04363808

Reaction notes

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