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

HRID 1902453Notes

Reaction equation

HRID 1902453 reaction equation
[N:1]1([CH2:10][CH2:11][CH2:12][NH2:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH2:14][C:15](=[O:28])[CH2:16][C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][CH:23]2[O:25][CH2:24]2)=[CH:19][CH:18]=1>CO>[NH2:14][C:15](=[O:28])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:21][CH2:22][CH:23]([OH:25])[CH2:24][NH: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:26][CH:27]=1

Participants

4

Reactant 2

HCID 1198572-(4-(2,3-Epoxypropoxy)phenyl)acetamideHCID 39208493-(1H-1,3-benzodiazol-1-yl)propan-1-amine

Product 1

HCID 13066756N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.8 grams of 1H-benzimidazole-1-propanamine and 12.16 grams of 1-[4-(2-amino-2-oxoethyl)phenoxy]-2,3-epoxypropane in 400 ml of 95% methanol was refluxed for 17 hours. The solvent was then evaporated under reduced pressure and the residue was chromatographed on a silica gel column packed in chloroform and eluted with solutions containing increasing percentages of methanol in chloroform. The fractions eluted with 30% methanol were combined and the solvent evaporated under reduced pressure. The solid residue was triturated with ether and then separated and dried at reduced pressure and room temperature to give N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine melting at about 92°-96° C. This compound has the following structural formula: ##STR12##

Workup

  1. temperaturewas refluxed for 17 hours
  2. customThe solvent was then evaporated under reduced pressure
  3. customthe residue was chromatographed on a silica gel column
  4. washeluted with solutions
  5. additioncontaining
  6. temperatureincreasing percentages of methanol in chloroform
  7. washThe fractions eluted with 30% methanol
  8. customthe solvent evaporated under reduced pressure
  9. customThe solid residue was triturated with ether
  10. customseparated
  11. customdried at reduced pressure and room temperature

Sources & evidence

ORD record
ord-088e7d0c1e6c484297f0c491156da639
Source dataset
uspto-grants-1982_12
Patent number
US04363808

Reaction notes

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