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Method for preparing (+/-)-norepinephrine

A technology of norepinephrine and reaction flask, which is applied in the field of chemical synthesis, can solve the problems of multiple by-products, reduced purity of final products, high requirements for hydrogenation equipment, etc., and achieves high product yield, low production cost, and low equipment requirements. Effect

Active Publication Date: 2013-08-28
苏州亚培克生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The commonly used hydrogenation method needs to pressurize the hydrogenation system, which has higher requirements on the hydrogenation equipment, and also produces more by-products, which reduces the purity of the final product

Method used

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  • Method for preparing (+/-)-norepinephrine
  • Method for preparing (+/-)-norepinephrine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 203.5g of 1-(3,4-dihydroxyphenyl)-2-aminoethanone hydrochloride and 770ml of water into a 2L reaction flask, heat to 55°C under stirring, transfer to a 2L hydrogenation flask, add Pd / C (Pd: 5%; water: 75%) 63.7g, control the internal temperature at 28°C, react with hydrogen at normal pressure for 18 hours, and filter. The filtrate was cooled to below 10°C, concentrated ammonia water was added, the pH value was adjusted to 9, filtered, and vacuum-dried to obtain 147.1 g of solid with a yield of 87.0% and a purity of 99.3% by HPLC.

Embodiment 2

[0019] Add 203.5g of 1-(3,4-dihydroxyphenyl)-2-aminoethanone hydrochloride and 770ml of water into a 2L reaction flask, heat to 55°C under stirring, transfer to a 2L hydrogenation flask, add Pd / C (Pd: 10%; Water: 75%) 35.1g, control the internal temperature at 35°C, react with hydrogen at normal pressure for 28 hours, and filter. The filtrate was cooled to below 10°C, concentrated ammonia water was added, the pH value was adjusted to 9, filtered, and vacuum-dried to obtain 144.1 g of solid, the yield was 85.3%, and the purity by HPLC was 99.1%.

Embodiment 3

[0021] Add 203.5g of 1-(3,4-dihydroxyphenyl)-2-aminoethanone hydrochloride and 770ml of water into a 2L reaction flask, heat to 55°C under stirring, transfer to a 2L hydrogenation flask, add Pd / C (Pd: 5%; water: 75%) 55.6g, control the internal temperature at 25°C, react with hydrogen at normal pressure for 20 hours, and filter. The filtrate was cooled to below 10°C, concentrated ammonia water was added, the pH value was adjusted to 10, filtered, and vacuum-dried to obtain 141.1 g of solid with a yield of 83.5% and a purity of 98.5% by HPLC.

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Abstract

The invention discloses a method for preparing (+ / -)-norepinephrine shown in a formula (II). The method comprises the following steps of: (a) adding water to dissolve 1-(3,4-dihydroxybenzene)-2-amino ethanone hydrochloride shown in a formula (I), shifting the obtained product into a hydrogenation bottle, adding a palladium-carbon catalyst, controlling reaction temperature to be between 10 and 45 DEG C, introducing hydrogen under normal pressure and performing reaction for 14 to 36 hours; and (b) filtering the obtained product after reaction is finished, regulating the pH of the obtained filtrate to be between 9 and 10 by using alkali, filtering the obtained product and performing vacuum drying on a filter cake to obtain the (+ / -)-norepinephrine. In the method, an amination intermediate (1-(3,4-dihydroxybenzene)-2-amino ethanone hydrochloride) is used as a raw material, and the (+ / -)-norepinephrine is obtained by introducing the hydrogen under normal pressure to perform reaction, so the method has the advantage of simple process, readily available raw material, low requirement on equipment, mild reaction conditions, implementation under normal pressure, high yield and purity of theproduct, few by-products, low production cost, suitability for industrial production and great application prospect.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of (±)-norepinephrine. Background technique [0002] Norepinephrine (Norepinephrine), scientific name 1-(3,4-dihydroxyphenyl)-2-aminoethanol, is a substance formed by removing the N-methyl group of adrenaline, molecular formula C 8 h 11 o 3 N, molecular weight 169.18, its structural formula is as follows: [0003] [0004] Norepinephrine is not only a neurotransmitter, mainly synthesized and secreted by sympathetic postganglionic neurons and adrenergic nerve endings in the brain, it is the main transmitter released by the latter, but also a hormone, synthesized and secreted by the adrenal medulla secreted, but in small amounts. Circulating norepinephrine comes primarily from the adrenal medulla. [0005] Medicinal norepinephrine is an adrenergic receptor agonist, which can constrict blood vessels and raise blood pressure. It is mainly used to rescue ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/60C07C213/00
Inventor 魏东初冯海涛周京仙
Owner 苏州亚培克生物科技有限公司