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

HRID 705157

Reaktionsgleichung

Reaktionsgleichung von HRID 705157
[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-2cc336777abc4b36a6be82a6f3f5443e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173879B2

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