α-溴代-3,4-二氯苯乙酮 → 1-(3,4-Dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanone

HRID 705157

反应方程式

HRID 705157 反应方程式
[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]

参与物

4

反应物 2

HCID 244751α-溴代-3,4-二氯苯乙酮HCID 5152225N-甲基-3-甲氧基苄胺

产物 1

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

试剂、催化剂与溶剂 1

HCID 8471三乙胺溶剂

实验过程

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.

来源与证据

ORD记录
ord-2cc336777abc4b36a6be82a6f3f5443e
来源数据集
uspto-grants-2015_11
专利号
US09173879B2

关联笔记

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