2-Bromo-1-(3,4-dichlorophenyl)ethanone → 1-(3,4-Dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanone

HRID 2409384

Reaktionsgleichung

Reaktionsgleichung von HRID 2409384
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][NH:10][CH3:11])[CH:6]=[CH:7][CH:8]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[Cl:23])[C:16](=[O:19])[CH2:17]Br>C(N(CC)CC)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:16](=[O:19])[CH2:17][N:10]([CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:11])[CH:20]=[CH:21][C:22]=1[Cl:23]

Komponenten

4

Edukt 2

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 51522253-Methoxy-N-methylbenzylamine

Produkt 1

HCID 595803421-(3,4-Dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

1-(3-Methoxyphenyl)-N-methylmethanamine is reacted with 3,4-dichlorophenacyl bromide in the presence of triethylamine to give 1-(3,4-dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanone. Reduction of this ketone by sodium borohydride yields 1-(3,4-dichlorophenyl)-2-(3-methoxybenzyl)(methyl)amino)ethanol, which undergoes acid mediated cyclization to give 4-(3,4-dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline. This racemic tetraisoquinoline derivative can be separated via chiral HPLC or supercritical fluid chromatography (SFC) to give the single enantiomers. Alternatively, the chiral separation can be achieved by recrystallization using chiral acids such as di-p-toluoyl-D-tartaric acid or di-p-toluoyl-L-tartaric acid.

Quellen und Nachweise

ORD-Eintrag
ord-92456561a4784d05848a41406376d673
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815894B2

Verknüpfte Notizen

Wird geladen…