Toluene → N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine

HRID 323965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323965
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C1(C)C=CC=CC=1>CC(N(C)C)=O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:12][CH2:11][C:10]([NH:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)([CH3:14])[CH3:13])=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 183497652-[3-(Imidazol-1-yl)propylamino]-2-methyl-1-propanol

Produkt 1

HCID 18349726N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A solution of 2-[3-(imidazol-1-yl)propylamino]-2-methyl-1-propanol (1.5 g) in dimethyl acetamide (10 ml) was added dropwise to a stirred suspension of sodium hydride (0.32 g of a 60% dispersion in mineral oil) in dimethyl acetamide (15 ml) at 30° C. under nitrogen. The mixture was stirred for 45 minutes at 30° C. and then a solution of 4-chlorobenzyl chloride (1.63 g) in dimethyl acetamide (5 ml) was added. After the addition, the mixture was heated at 100-105° C. for 30 minutes and then cooled to 25° C. Toluene (50 ml) was added and the mixture was washed with water. The toluene layer was extracted with 5M hydrochloric acid. The combined acid extracts were basified with concentrated sodium hydroxide solution with cooling and extracted with dichloromethane to give an oil which was distilled under high vacuum to give N-[2-(4-chlorobenzyloxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propylamine, b.p. 180-185° C. at 0.3 mbar.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was heated at 100-105° C. for 30 minutes
  3. temperaturecooled to 25° C
  4. washthe mixture was washed with water
  5. extractionThe toluene layer was extracted with 5M hydrochloric acid
  6. temperaturewith cooling
  7. extractionextracted with dichloromethane
  8. customto give an oil which
  9. distillationwas distilled under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f13bd58339324978a6c842ef6a00ce81
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06215001B1

Notizen zur Reaktion

Wird geladen…