6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride → n-[4-(6-Methoxy-3,4-dihydro-1h-isoquinolin-2-yl)-2,6-dimethyl-phenyl]-3,3-dimethylbutanamide

HRID 2067822

Reaktionsgleichung

Reaktionsgleichung von HRID 2067822
CC(C)([O-])C.[K+].Cl.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][NH:15][CH2:14][CH2:13]2.Br[C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([NH:28][C:29](=[O:35])[CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[C:23]([CH3:36])[CH:22]=1>C1(C)C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][N:15]([C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([NH:28][C:29](=[O:35])[CH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[C:23]([CH3:36])[CH:22]=1)[CH2:14][CH2:13]2

Komponenten

5

Edukt 3

HCID 29203356-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 23665647Potassium tert-butoxideHCID 59741059N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide

Produkt 1

HCID 24937331n-[4-(6-Methoxy-3,4-dihydro-1h-isoquinolin-2-yl)-2,6-dimethyl-phenyl]-3,3-dimethylbutanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (10 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (197 mg, 1.75 mmol), 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride salt (134 mg, 0.67 mmol) and N-(4-bromo-2,6-dimethyphenyl)-3,3-dimethylbutanamide (200 mg, 0.67 mmol) were then added and the reaction mixture was stirred at 80° C. overnight. The reaction mixture was then cooled to room temperature, concentrated, filtered through a pad of silica gel, and recrystallized from toluene to afford the title compound as a solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 80° C. overnight
  2. concentrationconcentrated
  3. filtrationfiltered through a pad of silica gel
  4. customrecrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-374e6db6053a449ea47c2fdeefb25ee4
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293911B2

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