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

HRID 2409384

Reaction equation

HRID 2409384 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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.

Sources & evidence

ORD record
ord-92456561a4784d05848a41406376d673
Source dataset
uspto-grants-2014_08
Patent number
US08815894B2

Linked notes

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