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

HRID 1388914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388914
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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##

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2a512def4f07427bb14d02d63853ed0f
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04434174

Notizen zur Reaktion

Wird geladen…