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

HRID 1902458Notes

Reaction equation

HRID 1902458 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]=1

Participants

4

Reactant 2

HCID 1198572-(4-(2,3-Epoxypropoxy)phenyl)acetamideHCID 132678794-(1H-Benzo[d]imidazol-1-yl)butan-2-amine

Product 1

HCID 13066759N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-alpha-methyl-1H-benzimidazole-1-propanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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##

Workup

  1. customThe solvent was evaporated from the mixture
  2. customthe residual solid was triturated several times with ether
  3. customThe solid was then dried
  4. customchromatographed on a silica gel column
  5. additionThe fractions containing the desired product
  6. customThe solvent was then evaporated
  7. customto leave a residual oil which
  8. temperatureon cooling

Sources & evidence

ORD record
ord-b4ccf944a61240c8a06996e82798dd43
Source dataset
uspto-grants-1982_12
Patent number
US04363808

Reaction notes

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