N-[(E)-(4-chlorophenyl)methylidene]-2-(3,4-dimethoxyphenyl)-1-ethanamine; N-[(E)-(4-chlorophenyl)methylidene]-N-(3,4-dimethoxyphenethyl)amine -Drug Synthesis Database

【结构式】

【分子编号】65051

【品名】N-[(E)-(4-chlorophenyl)methylidene]-2-(3,4-dimethoxyphenyl)-1-ethanamine; N-[(E)-(4-chlorophenyl)methylidene]-N-(3,4-dimethoxyphenethyl)amine

【CA登记号】

【分子式】C₁₇H₁₈ClNO₂

【分子量】303.78816

【元素组成】C 67.21% H 5.97% Cl 11.67% N 4.61% O 10.53%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

Condensation between 2-(3,4-dimethoxyphenyl)ethylamine (I) and 4-chlorobenzaldehyde (II) in refluxing toluene affords imine (III). Then, Pictet-Spengler cyclization of imine (III) in the presence of trifluoroacetic acid leads to the tetrahydroisoquinoline (IV). This is further acylated in boiling acetic anhydride to produce the target acetamide.

参考文献中间体

合成目标

【1】 Gitto, A.; Barreca, M.L.; De Luca, L.; De Sarro, G.; Ferreri, G.; Quartarone, S.; Russo, E.; Constanti, A.; Chimirri, A.; Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. J Med Chem 2003, 46, 1, 197.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	10098	2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine	120-20-7	C₁₀H₁₅NO₂	详情	详情
(II)	29029	4-chlorobenzaldehyde	104-88-1	C₇H₅ClO	详情	详情
(III)	65051	N-[(E)-(4-chlorophenyl)methylidene]-2-(3,4-dimethoxyphenyl)-1-ethanamine; N-[(E)-(4-chlorophenyl)methylidene]-N-(3,4-dimethoxyphenethyl)amine		C₁₇H₁₈ClNO₂	详情	详情
(IV)	65052	1-(4-chlorophenyl)-6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether; 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline		C₁₇H₁₈ClNO₂	详情	详情

Extended Information