A kind of method for preparing primaquine phosphate

A technology of primaquine phosphate and aminoquinoline, which is applied in organic chemistry and other fields, and can solve problems such as the limitation of intermediate yields

Active Publication Date: 2015-08-19
HUNAN FURUI BIOPHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The important intermediate N-(4-bromopentane)-phthalimide in the known synthetic route needs to be prepared by multi-step reaction, so the yield of this intermediate is greatly limited

Method used

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  • A kind of method for preparing primaquine phosphate
  • A kind of method for preparing primaquine phosphate
  • A kind of method for preparing primaquine phosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (1) Reaction of methyl vinyl ketone with nitromethane

example 1

[0052] Add 8.0 ml (0.1 mol) of methyl vinyl ketone, 32 ml (0.6 mol) of nitromethane and 4.0 g of basic alumina-supported potassium fluoride catalyst into 80 ml of ethanol and stir at room temperature for 24 hours. After the reaction was finished, the insolubles were removed by suction filtration, ethanol and excess nitromethane were distilled off under normal pressure, and the 5-nitropentan-2-one (compound of formula I) distilled under reduced pressure was 11.2 g of light yellow oily matter. The rate is 87%. The proton NMR spectrum of the product (see the attached figure 1 ): 1 H NMR (400MHz, CDCl 3 )δ=4.42(t,J=6.6Hz,2H),2.60(t,J=6.8Hz,2H),2.26-2.19(m,2H),2.15(s,3H).

example 2

[0054] The scale of the reaction in Example 1 was expanded to 100 ml of methyl vinyl ketone, and other materials were expanded in proportion. After 24 hours of reaction, 119 grams of 5-nitropentan-2-one were distilled under reduced pressure, with a yield of 92.7%.

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Abstract

The invention relates to a method for preparing primaquine diphosphate. The method comprises the following steps: enabling methyl vinyl ketone and nitromethane to react to prepare 5-amylnitrite-2-ketone; then carrying out a condensation reaction on the 5-amylnitrite-2-ketone and 6-methoxyl-8-aminoquinoline to generate an imine intermediate product; carrying out a reduction reaction on the obtained imine intermediate product to generate primaquine; and acidifying to form salt by using phosphoric acid, and the like. According to the method disclosed by the invention, a primaquine diphosphate finished product can be obtained by recrystallizing the obtained primaquine diphosphate. Due to the adoption of the new synthetic route disclosed by the invention, the primaquine phosphate can be fast obtained from common industrial raw materials.

Description

technical field [0001] The invention relates to a method for preparing primaquine phosphate. Background technique [0002] Primaquine phosphate is orange-red crystalline powder, odorless, bitter taste, soluble in water but insoluble in chloroform and ether, its English name is Primaquine diphosphate, Chinese name is N4-(6-methoxy-8-quinolinyl )-1-pentanediamine diphosphate, aliased as primaquine phosphate, paramaquine, and primaquinoline phosphate. Molecular formula is C 15 h 21 N 3 O·2H 3 PO 4 , molecular weight 455.34. Its pharmacological effect is to inhibit the activity of coenzyme Q, block the electron transfer in the mitochondria of Plasmodium, and thus inhibit the oxidative phosphorylation process of Plasmodium. It has a strong killing effect on the delayed extraerythrocytic spores and gametophytes of Plasmodium vivax, so it is called an antimalarial drug in the industry. [0003] The preparation of known primaquine phosphate usually adopts the condensation of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/40
Inventor 曾步兵任江萌
Owner HUNAN FURUI BIOPHARMA TECH CO LTD
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