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Preparation method and preparation device of deuterated low-carbon amine

A preparation device and deuterium technology are applied in the preparation field of chemical drug intermediates, which can solve the problems of difficulty in purchasing, large amount, high cost, etc., and achieve the effects of convenient quantification and subsequent operations, low moisture content, and high production efficiency.

Pending Publication Date: 2021-12-14
安徽昊帆生物有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, free deuterated lower carbon amines are gaseous at room temperature and must be stored in pressure tanks before they can be transported and used
In use, there are problems such as low safety and difficulty in quantification
In addition, deuterated low-carbon amine compounds are flammable gases, which are controlled chemicals, and there are no domestic suppliers, making it difficult to purchase
[0007] At present, deuterated low-carbon amine compounds obtained commercially are usually inorganic acid salts such as hydrochloric acid or sulfuric acid, and the price is expensive. If they are used directly as amination reagents, the dosage is large, the conversion rate is low, and the recovery is difficult and the cost is high.

Method used

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  • Preparation method and preparation device of deuterated low-carbon amine

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preparation example Construction

[0069] The preparation method of the deuterated lower carbon amine according to the embodiment of the present invention comprises:

[0070] Step S1, providing an inorganic acid salt solution of deuterated lower carbon amine;

[0071] Step S2, reacting the inorganic acid salt solution of the deuterated lower amine with a solid base to obtain the deuterated lower amine.

[0072] In combination with the above-mentioned preparation device, that is: through the constant pressure dropping funnel 2, dropwise add the inorganic acid salt solution of deuterated lower carbon amine to the three-necked bottle 1, so that the inorganic acid salt solution of deuterated lower carbon amine and the three-necked bottle 1 The solid base reacts to obtain free deuterated lower carbon amine.

[0073] This preparation method, for example, can be used to prepare the following deuterated lower amines: methyl-d 3 -amine, dimethyl-d 6 -amine, N-methyl-N-methyl-d 3 -amine,ethyl-d 5 -amine, diethyl-d ...

Embodiment 1

[0086] At room temperature, 2.0 g of methyl-d was dissolved using a constant pressure dropping funnel 3 - 5mL of deionized aqueous solution of amine hydrochloride, dripped on the flaky NaOH solid in the 25mL three-necked flask, a large amount of methyl-d will be produced immediately 3 - Amine gas.

[0087] in N 2 Carried by a carrier gas, methyl-d 3 - The amine gas passes through the gas dryer filled with granular KOH desiccant. After removing moisture, it enters the gas condensing device. It is cooled and liquefied in the micro-Dewar condenser with dry ice as the coolant. It is dropped into the dry ice-acetone Store in a 10 mL collector in the bath.

[0088] Weigh at low temperature and collect liquid methyl-d 3 -Amine 0.78g, yield: 80.4%.

Embodiment 2

[0090] At room temperature, 5.0 g of methyl-d was dissolved using a constant pressure dropping funnel 3 - 15mL deionized aqueous solution of amine sulfate, drop on the flaky KOH solid in the 50mL three-necked flask, a large amount of methyl-d will be produced immediately 3 - Amine gas.

[0091] in N 2 Carried by a carrier gas, methyl-d 3 - The amine gas passes through the gas dryer filled with granular KOH desiccant. After removing moisture, it enters the gas condensing device. It is cooled and liquefied in the micro-Dewar condenser with dry ice-ethanol as the coolant, and dropped into the liquid Store in a 10 mL collector in a nitrogen-acetone bath.

[0092] Weigh at low temperature and collect liquid methyl-d 3 -Amine 1.90g, yield: 92.7%.

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Abstract

The invention provides a preparation method and a preparation device of deuterated low-carbon amine, and the preparation method comprises the following steps: S1, providing an inorganic acid salt solution of the deuterated low-carbon amine; and s2, enabling the inorganic acid salt solution of the deuterated low-carbon amine to react with solid alkali to obtain the deuterated low-carbon amine. According to the preparation method disclosed by the embodiment of the invention, the obtained free deuterated low-carbon amine is high in purity, the process is simple, the production efficiency is high, the universality is good, and the preparation method is particularly suitable for preparing trace and semi-trace free deuterated low-carbon amine.

Description

technical field [0001] The invention relates to the technical field of preparation of chemical drug intermediates, in particular to a preparation method and a preparation device of a deuterated lower carbon amine. Background technique [0002] Deuterium (deuterium, D) replaces some H atoms in the drug molecule, and the obtained deuterated drug can block the relevant metabolic sites of the drug without affecting the original biological activity of the drug, thereby reducing the production of toxic metabolites. Generate, prolong drug half-life, reduce single dose (Pirali T, Serafini M, Cargnin S, Genazzani AA. Applications of deuterium in medicinal chemistry[J]. Journal of Medicinal Chemistry, 2019, 62(11): 5276-5297. ). Deutemled drug molecules: focus on FDA-approved deutetrabenazine [J]. Biochemistry, 2018, 57(5):472-473.). [0003] The lower carbon amine group is a common substituent group in drug molecules, and it is also a key metabolic site in some drug molecules. Re...

Claims

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Application Information

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IPC IPC(8): C07C209/00C07C211/04C07C211/05B01J19/00
CPCC07C209/00B01J19/00C07B2200/05C07C211/04C07C211/05
Inventor 陆雪根李宏林
Owner 安徽昊帆生物有限公司
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