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4-n-substituted-1-(3-methoxypropyl)-4-piperidinamine compounds and their preparation and application

A technology of methoxypropyl and piperidinamine, applied in the application field of synthesizing prucalopride succinate, achieving the effect of convenient preparation

Inactive Publication Date: 2016-01-20
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no bibliographical report on the synthesis of compound 4 at present, therefore, it will be of great significance to find a synthetic method of compound 4

Method used

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  • 4-n-substituted-1-(3-methoxypropyl)-4-piperidinamine compounds and their preparation and application
  • 4-n-substituted-1-(3-methoxypropyl)-4-piperidinamine compounds and their preparation and application
  • 4-n-substituted-1-(3-methoxypropyl)-4-piperidinamine compounds and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of 4-N-tert-butoxycarbonyl-1-(3-methoxypropyl)-4-piperidinamine (1-1)

[0041] Add 4-Boc-aminopiperidine (30.04g, 0.15mol), 1-bromo-3-methoxypropane (22.95g, 0.15mol), potassium carbonate (20.73g, 0.15mol) and acetonitrile in a 1000ml reaction flask (500ml), reflux for 5h, concentrate under reduced pressure, add water (200ml) and stir, filter, wash the filter cake with water (100ml), and dry to obtain off-white solid 4-N-tert-butoxycarbonyl-1-(3-methyl Oxypropyl)-4-piperidinamine (39.11 g, yield 95.85%), melting point 72.5-73.5°C.

[0042] MS (m / z): 273.22 ([M+H] + )

[0043] 1 H-NMR (400MHz, DCCl 3 )δ: 1.41 (9H, s), 1.59 (2H, m), 1.60-1.86 (4H, m), 2.43-2.53 (6H, m), 3.36 (3H, s), 3.42 (2H, t), 3.63 (1H, m).

Embodiment 2

[0045] Preparation of 1-(3-methoxypropyl)-4-piperidinamine (4)

[0046] 4-N-tert-butoxycarbonyl-1-(3-methoxypropyl)-4-piperidinamine (39.11g, 0.144mol), concentrated hydrochloric acid (250ml) and ethanol (500ml) were added to the reaction flask, room temperature After reacting for 3h, NaOH (20g) in ethanol (200ml) was added after concentration under reduced pressure. After concentration, dichloromethane (200ml) was added, filtered, and the filtrate was concentrated to give light yellow oil 4 (21.75g, yield 87.9%).

[0047] MS (m / z): 173.18 ([M+H]+)

Embodiment 3

[0049] Preparation of 4-N-benzyloxycarbonyl-1-(3-methoxypropyl)-4-piperidinamine (1-2)

[0050] 4-Cbz-aminopiperidine (23.43g, 0.1mol), 1-bromo-3-methoxypropane (15.30g, 0.1mol), potassium carbonate (8.30g, 0.1mol) and acetone (250ml) were added to 500ml In the reaction flask, reflux for 5h. Concentrate under reduced pressure, add water, stir, filter, and dry to give white solid 4-N-benzyloxycarbonyl-1-(3-methoxypropyl)-4-piperidinamine (24.97 g, 81.49%).

[0051] MS (m / z): 307.21 ([M+H]+)

[0052] 1H-NMR (400MHz, DCCl3) δ: 1.59 (2H, m), 1.62-1.85 (4H, m), 2.43-2.53 (6H, m), 3.36 (3H, s), 3.42 (2H, t), 3.63 (1H, m), 5.16 (2H, s), 7.30-7.51 (5H, m).

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Abstract

The invention provides a 4-N-substituted-1-(3-methoxypropyl)-4-piperidinamine compound and its preparation and application. The 4-N-substituted-1-(3-methyl Oxypropyl)-4-piperidinamine compounds can be conveniently used to prepare the key intermediate of prucalopride succinate, so that prucalopride succinate can be prepared conveniently, and can meet the needs of the pharmaceutical industry. 4-N-substituted-1-(3-methoxypropyl)-4-piperidinamine compounds are free bases or salts thereof represented by the formula (1): .

Description

technical field [0001] The invention relates to a 4-N-substituted-1-(3-methoxypropyl)-4-piperidinamine compound and its application in the synthesis of prucalopride succinate. Background technique [0002] Prucalopride succinate chemical name: N-[1-(3-methoxypropyl)-4-piperidinyl]-4-amino-5-chloro-2,3-dihydrobenzofuran-7 - Formamide succinate, developed by Janssen Company in Belgium, is a highly selective and specific 5-HT 4 Receptor agonist, which was launched in the UK in 2010, is used to treat female patients with constipation who are ineffective on laxatives. Its structural formula is as follows: [0003] [0004] With the rapid economic development, the extreme deterioration of the ecological environment and the acceleration of people's life rhythm, constipation has become a common problem in the society, and the prevalence rate is increasing year by year. It seriously affects the quality of life of patients. Patients may be accompanied by dizziness, dizziness, nau...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/58C07D405/12
Inventor 李建其廖云凤翁志洁
Owner SHANGHAI INST OF PHARMA IND CO LTD
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