3,4-dimethoxyphenylamine; 3,4-dimethoxyaniline -Drug Synthesis Database

【结构式】

【分子编号】18935

【品名】3,4-dimethoxyphenylamine; 3,4-dimethoxyaniline

【CA登记号】6315-89-5

【分子式】C₈H₁₁NO₂

【分子量】153.18088

【元素组成】C 62.73% H 7.24% N 9.14% O 20.89%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

3-Chloropropionyl chloride (II) was condensed with 4-aminoveratrole (I) in the presence of triethylamine to give the chloropropionamide (III). Further alkylation of N-methyl-2-(3,4-dimethoxyphenyl)ethylamine (IV) with (III) in refluxing acetonitrile afforded the aminopropionamide (V), which was subsequently reduced to diamine (VI) with LiAlH4 in boiling THF. Finally, acylation of (VI) with 4-nitrobenzoyl chloride (VII) gave the target amide.

参考文献中间体

合成目标

【1】 Nadler, G.; Faivre, J.F.; Forest, M.C.; Cheval, B.; Martin, M.; Souchet, M.; Gout, B.; Bril, A.; Synthesis, electrophysiological properties and analysis of structural requirements of a novel class of antiarrhythmic agents with potassium and calcium channel blocking properties. Bioorg Med Chem 1998, 6, 11, 1993.

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)	18935	3,4-dimethoxyphenylamine; 3,4-dimethoxyaniline	6315-89-5	C₈H₁₁NO₂	详情	详情
(II)	18936	3-chloropropanoyl chloride	625-36-5	C₃H₄Cl₂O	详情	详情
(III)	18937	3-chloro-N-(3,4-dimethoxyphenyl)propanamide		C₁₁H₁₄ClNO₃	详情	详情
(IV)	18938	2-(3,4-dimethoxyphenyl)-N-methyl-1-ethanamine; N-(3,4-dimethoxyphenethyl)-N-methylamine	3490-06-0	C₁₁H₁₇NO₂	详情	详情
(V)	18939	3-[(3,4-dimethoxyphenethyl)(methyl)amino]-N-(3,4-dimethoxyphenyl)propanamide		C₂₂H₃₀N₂O₅	详情	详情
(VI)	18940	N(1)-(3,4-dimethoxyphenethyl)-N(3)-(3,4-dimethoxyphenyl)-N(1)-methyl-1,3-propanediamine; N-[3-(3,4-dimethoxyanilino)propyl]-N-(3,4-dimethoxyphenethyl)-N-methylamine		C₂₂H₃₂N₂O₄	详情	详情
(VII)	18941	p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride	122-04-3	C₇H₄ClNO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Alkylation of hydroxylamine with propargyl bromide (I) provided N-propargyl hydroxylamine (II), which was subsequently acylated with 3-chloropropionyl chloride (III) in the presence of pyridine to yield the N-hydroxy amide (IV). Mannich reaction of the propargyl compound (IV) with paraformaldehyde and pyrrolidine (V) with simultaneous cyclization of the N-hydroxy chloropropionamide furnished the title compound.

参考文献中间体

合成目标

【1】 Amstutz, R.; et al.; Position 5 at the oxotremorinic skeleton as the stearing position for activity at the muscarinic receptors. Helv Chim Acta 1987, 70, 2232.

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)	11176	3-Bromopropyne; 3-Bromo-1-propyne	106-96-7	C₃H₃Br	详情	详情
(II)	50918	3-(hydroxyamino)-1-propyne; N-(2-propynyl)hydroxylamine		C₃H₅NO	详情	详情
(III)	18935	3,4-dimethoxyphenylamine; 3,4-dimethoxyaniline	6315-89-5	C₈H₁₁NO₂	详情	详情
(IV)	50919	3-chloro-N-hydroxy-N-(2-propynyl)propanamide		C₆H₈ClNO₂	详情	详情
(V)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情

Extended Information