2-(4-(2,3-Epoxypropoxy)phenyl)acetamide → HCID 13066756, compound

HRID 1388910Notes

Reaction equation

HRID 1388910 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1CCCN.[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:27]=[CH:26][C:20]([O:21][CH2:22][CH:23]([OH:25])[CH2:24][NH:1][CH2:5][CH2:4][CH2:9][N:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=[CH:2]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 1198572-(4-(2,3-Epoxypropoxy)phenyl)acetamideHCID 17131513-(1H-1,3-benzodiazol-2-yl)propan-1-amine

Product 1

HCID 13066756HCID 13066756, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.8 grams of 1H-benzimidazole-2-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-e760b068a3f544cb8a8e95c1d053b76a
Source dataset
uspto-grants-1984_02
Patent number
US04434174

Reaction notes

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