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【结 构 式】

【药物名称】Propiram fumarate, Bay-4503, Dirame, Algeril

【化学名称】N-[1-Methyl-2-(1-piperidinyl)ethyl]-N-(2-pyridyl)propanamide (E)-2-butenedioate (1:1)

【CA登记号】13717-04-9, 15686-91-6 (free base)

【 分 子 式 】C20H29N3O5

【 分 子 量 】391.47123

【开发单位】Bayer (Originator), Shire Pharmaceuticals (Licensee)

【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Opioid Analgesics, mu-Opioid Agonists, mu-Opioid Antagonists

合成路线1

The reduction of 1-(1-piperdinyl)acetone oxime (I) with LiAlH4 in ethyl ether, THF or dioxan gives 1-methyl2-(1-piperidinyl)ethylaine (II), which is acylated with propionyl chloride (III) in ether to afford propionamide (IV). The condensation of (IV) with 2-bromopyridine (V) by heating with K2CO3 and Cu (dust) provides compound (VI). Alternatively, (VI) can be obtained by heating N-[1-methyl-2-(1-piperidinyl)ethyl]-N-(2-pyridyl)amine (VII) with propionic anhydride (VIII). Finally, heating derivative (VI) with fumaric acid in acetone/EtOH allows formation of the desired compound as the corresponding fumarate salt.

1 (Almirall Prodesfarma, SA); Process for the preparation of 2-aminopyridine derivs.. ES 434325 .
2 Hoffmeister, F.; Wirth, W.; Kroneberg, H.-G.; Hiltmann, R.; Wollweber, H. (Bayer AG); Pyridine derivs. and their preparation (-N-tertiaryl aminoalkyl-N-acyl)amino pyridines. DE 1232147; US 3163654 .
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) 47242 1-(1-piperidinyl)acetone oxime C8H16N2O 详情 详情
(II) 47243 1-methyl-2-(1-piperidinyl)ethylamine; 1-(1-piperidinyl)-2-propanamine C8H18N2 详情 详情
(III) 15967 propanoyl chloride; propionyl chloride 79-03-8 C3H5ClO 详情 详情
(IV) 47244 N-[1-methyl-2-(1-piperidinyl)ethyl]propanamide C11H22N2O 详情 详情
(V) 29052 2-Bromopyridine;α-bromopyridine;α-bromoazine 109-04-6 C5H4BrN 详情 详情
(VI) 47245 N-[1-methyl-2-(1-piperidinyl)ethyl]-N-(2-pyridinyl)propanamide C16H25N3O 详情 详情
(VII) 47246 N-[1-methyl-2-(1-piperidinyl)ethyl]-2-pyridinamine; N-[1-methyl-2-(1-piperidinyl)ethyl]-N-(2-pyridinyl)amine C13H21N3 详情 详情
(VIII) 20095 propionic anhydride 123-62-6 C6H10O3 详情 详情
Extended Information