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Preparation method of 2-substituted-4-(piperidylmethyl) pyridine

A technology of hydroxymethylpyridine and methylmethyl, which is applied in the field of preparation of 2-substituted-4-(piperidinylmethyl)pyridine, can solve the problem of high toxicity to production operators, high requirements for reaction equipment, serious environmental pollution, etc. problems, to achieve the effect of helping environmental protection, less side reactions, and low selection requirements

Active Publication Date: 2014-04-09
双鹤药业(海南)有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1) using phosphorus tribromide as a reaction reagent, which is highly corrosive and seriously pollutes the environment, and has high requirements for reaction equipment; and
[0007] 2) Intermediate 3 has a benzyl bromide structure, is extremely toxic, has strong allergies, and is highly toxic to production operators;

Method used

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  • Preparation method of 2-substituted-4-(piperidylmethyl) pyridine
  • Preparation method of 2-substituted-4-(piperidylmethyl) pyridine
  • Preparation method of 2-substituted-4-(piperidylmethyl) pyridine

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Embodiment Construction

[0051] 1. Preparation of N-chlorodiisopropylamine (Chem.Ber.1966,99:1347)

[0052] At 0°C, add 500 milliliters of diisopropylamine dropwise to 1 liter of 6.5% sodium hypochlorite solution. After the dropping is complete, raise the temperature naturally and stir for 1 hour. Separate the organic phase and wash it twice with 1N sulfuric acid. After sodium drying, the desiccant was filtered off to obtain 362 g, yield 75%. 1 H NMR (CDCl 3): δ 1.18 (d, J = 6.0 Hz, 12H), 3.29 (m, 2H).

[0053] 2. Preparation of 2-bromo-4-(piperidinylmethyl)pyridine (Formula 1, R=Br)

[0054] Dissolve 171.3 grams of 2-bromo-4-hydroxymethylpyridine (formula 2, R=Br), 356 grams of triphenylphosphine and 700 milliliters of tetrahydrofuran in a 2L three-necked flask, then add 90.3 milliliters of piperidine, and cool in an ice-water bath to At 10°C, a solution of 133 g of N-chlorodiisopropylamine in 300 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for 4 ho...

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Abstract

The invention relates to a preparation method of 2-substituted-4-(piperidylmethyl) pyridine. The method comprises the following step of: making 2-substitute-4-hydroxymethylpyridine (2) serving as a raw material react with piperidine in an organic solvent under the action of an N-halogenated amine reagent and triphenylphosphine to directly generate 2-substituted-4-(piperidylmethyl) pyridine. Compared with the conventional method, the preparation method provided by the invention has multiple advantages.

Description

technical field [0001] The present invention relates to a new chemical synthesis method, more specifically to a new chemical method for preparing 2-substituted-4-(piperidinylmethyl)pyridine. Background technique [0002] Peptic ulcer disease is a common and frequently-occurring disease. At present, the main therapeutic drugs for peptic ulcer include proton pump inhibitors, H2 receptor antagonists, gastric mucosal protective agents and antacids. Lafutidine is a potent, long-acting second-generation histamine H developed jointly by Fujirebio and Taiho. 2 Receptor antagonist, can reduce the basal secretion of gastric acid, inhibit gastric acid secretion stimulated by histamine, gastrin, and urethane, and has a unique gastric protection effect. The drug was launched in Japan in April 2000 and is mainly used to treat peptic ulcer. Compared with other similar drugs (such as cimetidine and famotidine), the compound has a 2 The blocking effect of the receptor is more effective an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61C07D405/12C07D401/12
Inventor 周宜遂苏新海张平梅王建民李如兴
Owner 双鹤药业(海南)有限责任公司