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Synthetic method of prucalopride intermediate 1-(3-methoxy propyl)-4-piperidylamine

A technology of methoxypropyl and prucalopride, applied in the directions of organic chemistry, bulk chemical production, etc., to achieve the effects of avoiding operational danger, high yield and purity, and easy operation

Pending Publication Date: 2022-05-27
LUNAN PHARMA GROUP CORPORATION
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0044] Aiming at the many problems existing in the current synthesis of prucalopride related intermediate 1-(3-methoxypropyl)-4-piperidinamine, the invention provides a new 1-(3-methoxy The synthetic method of propyl)-4-piperidinamine

Method used

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  • Synthetic method of prucalopride intermediate 1-(3-methoxy propyl)-4-piperidylamine
  • Synthetic method of prucalopride intermediate 1-(3-methoxy propyl)-4-piperidylamine
  • Synthetic method of prucalopride intermediate 1-(3-methoxy propyl)-4-piperidylamine

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Experimental program
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Effect test

Embodiment 1

[0076] 4-Hydroxypiperidine (40.46g, 0.40mol), 3-bromopropylmethyl ether (X=Br, 79.57g, 0.52mol), potassium carbonate (88.45g, 0.64mol) were added to acetonitrile (400ml), The temperature was controlled at 75 to 80 °C to react, and after the reaction was detected, filtered, the filtrate was concentrated to dryness under reduced pressure, dichloromethane (500 ml) was added, washed with 1M dilute hydrochloric acid (150 ml) for 1 to 2 times, the organic layer was dried, and the pressure was reduced. Concentrated to obtain intermediate I-1 with a yield of 96.4% and a purity of 99.3%.

Embodiment 2

[0078] 4-Hydroxypiperidine (40.45g, 0.40mol), 3-iodopropyl methyl ether (X=I, 88.01g, 0.44mol), triethylamine (64.76g, 0.64mol) were added to N,N-diethylamine In methylformamide (400ml), the temperature is controlled to react at 80-85°C. After detection, the reaction is completed, filtered, the filtrate is concentrated to dryness under reduced pressure, dichloromethane (500ml) is added, and 2M dilute hydrochloric acid (150ml) is used to wash 1~ twice, the organic layer was dried and concentrated under reduced pressure to obtain intermediate I-1 with a yield of 93.7% and a purity of 99.4%.

Embodiment 3

[0080] 4-Hydroxypiperidine (40.43g, 0.40mol), 3-chloropropyl methyl ether (X=Cl, 64.82g, 0.60mol), sodium bicarbonate (53.76g, 0.64mol) were added to butanone (400ml) In the reaction, the temperature was controlled at 75-80 °C, and after the reaction was detected, the filtrate was filtered, and the filtrate was concentrated to dryness under reduced pressure. Dichloromethane (500ml) was added, washed with 0.5M dilute hydrochloric acid (150ml) for 1 to 2 times, and the organic layer was dried. , concentrated under reduced pressure to obtain intermediate I-1 with a yield of 95.9% and a purity of 98.1%.

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthetic method of a prucalopride intermediate 1-(3-methoxy propyl)-4-piperidylamine. According to the method, 4-hydroxypiperidine which is low in price and easy to obtain is used as a reaction raw material and reacts with urotropine after chlorination to construct amino, the compound 1-(3-methoxy propyl)-4-piperidylamine is prepared, the preparation method is safe and simple to operate, high in atom utilization rate, mild in reaction condition and environmentally friendly, the prepared target product has high yield and purity, and the method is suitable for industrial production. The method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a method for synthesizing prucalopride intermediate 1-(3-methoxypropyl)-4-piperidinamine. Background technique [0002] Prucalopride Succinate, chemical name is 4-amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl ]-7-benzofurancarboxamide succinate, is a new generation of high-selectivity, high-affinity serotonin 4(5-HT developed by Belgian Movetis Company 4 ) receptor agonists, which restore impaired intestinal motility by direct action on the intestinal wall. It was approved by the European Union for the treatment of chronic constipation in October 2009, launched in Germany in January 2010, in the UK in March of the same year, and approved by the FDA in October 2012. Clinical studies have shown that the drug has a constant and safe effect on patients with severe chronic constipation. . Its chemical structure is as follows: [0003] [0004] At presen...

Claims

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Application Information

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IPC IPC(8): C07D211/58
CPCC07D211/58Y02P20/55
Inventor 张乃华朱安国
Owner LUNAN PHARMA GROUP CORPORATION
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