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【结 构 式】 
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【分子编号】35289 【品名】3-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzaldehyde 【CA登记号】 |
【 分 子 式 】C18H15NO4 【 分 子 量 】309.32144 【元素组成】C 69.89% H 4.89% N 4.53% O 20.69% |
合成路线1
该中间体在本合成路线中的序号：(III)The alkylation of 3-hydroxybenzaldehyde (I) with N-(3-bromopropyl)phthalimide (II) in the presence of NaOMe leads to 3-(phthalimidopropoxy)benzaldehyde (III). The reductive alkylation of piperidine with aldehyde (III) in the presence of formic acid gives N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]phthalimide (IV), which is converted to N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amine (V) by treatment with 6N HCl. Condensation of (V) with glycolic acid in boiling xylene provides N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-2-hydroxyacetamide (VI), which is complexed with bismuth (+3) citrate (VII) in boiling water.
| 【1】 Petkov, O.; Lytakov, G.; Taskov, M.; Savov, E.; Kostev, V.; Tsvetkova, E.; Nikolov, G.; Atanassova, R.; Ivanov, C.; Synthesis, gastroprotective, antisecretory and anti-Helicobacter effect of +[3(3-(1-piperidinylmethyl)phenoxy)propyl]hydroxyacetamide-2-hydroxypropane-1,2,3-tricarboxylate-bismuth(3+) complex (MX1). J Pharm Pharmacol 1996, 3, 3, 297-301. |
| 【2】 N-(3-(3-(1-Piperidinylmethyl)phenoxy)propyl)propenetricarboxylate bismuth (3+) complex and the method for preparation. WO 9509162 . |
| 【3】 Mondeshka, D.; Spassov, G.; Krushkov, I.; Ivanov, C.; Marazova, K.; Roxatidine Bismuth Citrate. Drugs Fut 2000, 25, 5, 462. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10158 | Piperidine | 110-89-4 | C5H11N | 详情 | 详情 | |
| (I) | 28537 | 3-hydroxybenzaldehyde | 100-83-4 | C7H6O2 | 详情 | 详情 |
| (II) | 15216 | N-(3-Bromopropyl)phthalimide; 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione | 5460-29-7 | C11H10BrNO2 | 详情 | 详情 |
| (III) | 35289 | 3-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzaldehyde | C18H15NO4 | 详情 | 详情 | |
| (IV) | 35290 | 2-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione | C23H26N2O3 | 详情 | 详情 | |
| (V) | 16105 | 3-[3-(piperidinomethyl)phenoxy]-1-propanamine; 3-[3-(piperidinomethyl)phenoxy]propylamine | C15H24N2O | 详情 | 详情 | |
| (VI) | 29857 | 2-hydroxy-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]acetamide | C17H26N2O3 | 详情 | 详情 | |
| (VII) | 13855 | bismuth(3+) 2-hydroxy-1,2,3-propanetricarboxylate; Bismuth Citrate | 813-93-4 | C6H5BiO7 | 详情 | 详情 |