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A kind of synthetic method of desvenlafaxine succinate

A technology of desvenlafaxine succinate and compounds, which is applied in the field of drug synthesis, can solve problems such as unfavorable industrial operations, and achieve the effects of convenient operation, high synthesis yield, and good product purity

Active Publication Date: 2016-02-10
NANJING HUAWE MEDICINE TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] In this type of method, the former uses the unstable compound n-butyllithium and lithium aluminum hydride in the condensation and amide reduction reaction steps respectively; the latter uses the unstable compound hexamethyldisilazide lithium, Borane, the two-step reaction needs to be carried out under inert gas, and dangerous reagents are used twice, which is not conducive to industrial operation

Method used

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  • A kind of synthetic method of desvenlafaxine succinate
  • A kind of synthetic method of desvenlafaxine succinate
  • A kind of synthetic method of desvenlafaxine succinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of compound formula III

[0042] At room temperature, add compound formula II (81.69 g, 0.60 mol) and 1200 mL of acetone into a 3 L reaction flask, and stir to dissolve. Add K to it 2 CO 3 (265.36g, 1.92mol) was stirred, slowly added dropwise (112.88g, 0.65mol) benzyl bromide, heated and refluxed for 1h, cooled to room temperature after the reaction of the raw materials and suction filtered, the filter cake was washed with an appropriate amount of acetone, and the filtrate was spin-dried, 50°C Drying by blowing air gave 134.7 g of compound formula III with a yield of 99%. 1 HNMR (300MHz, DMSO): δ7.50-7.22 (m, 7H), δ6.93 (d, 2H), δ5.03 (s, 2H), δ2.53 (s, 3H); 13 C-NMR: δ 197.02, δ 163.42, δ 136.51, δ 129.83, δ 129.02, δ 128.91, δ 127.64, δ 127.10, δ 114.29, δ 70.13, δ 26.6.

Embodiment 2

[0044] According to the experimental operation of Example 1, benzyl bromide (112.88g, 0.65mol) was replaced by benzyl chloride (82.28g, 0.65mol), and the temperature was raised to reflux overnight. After the reaction was complete, it was cooled to room temperature and suction filtered. The filter cake was washed with an appropriate amount of acetone After washing, the filtrate was spin-dried and air-dried at 50° C. to obtain 103.17 g of compound formula III with a yield of 76%.

Embodiment 3

[0046] Synthesis of compound formula IV

[0047] In 3L reaction bottle, add compound formula III (67.9g, 0.30mol), CuBr 2 (147.4g, 0.65mol), 0.9L dichloromethane, 1.35LEA, heat up to reflux, cool and suction filter after the reaction is complete, and wash the filter cake with 200mL dichloromethane. Combine the filtrates, wash the filtrate with hydrochloric acid, wash with water twice, dry, spin dry, and blow dry at 50°C overnight. 89.43 g of the crude product of compound formula IV was obtained, with a yield of 98%.

[0048] Add 89.43g of compound formula IV (crude) into a 1L three-neck round bottom flask, recrystallize from isopropanol, filter with suction, and dry the filter cake with air blowing at 45°C. Refined product 84.9g, yield 95%. 1 HNMR (300MHz, DMSO-d 6 ): δ7.53-7.20(m, 7H), δ6.95(d, 2H), δ5.09(s, 2H), δ4.69(s, 2H); 13 C-NMR: δ 190.83, δ 164.12, δ 136.71, δ 129.96, δ 128.91, δ 128.31, δ 127.00, δ 126.73, δ 114.37, δ 70.82, δ 32.45.

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Abstract

The invention belongs to the field of the pharmaceutical chemistry, and concretely relates to a synthetic method of desvenlafaxine succinate. The method comprises the following steps: benzylating, halogenating, aminolyzing, reducing, carrying out hydroxy halogenations, condensing, carrying out a debenzylation reaction, and carrying out a reaction on the above obtained product, succinic acid and water to synthesize desvenlafaxine succinate (represented by formula I). The method has the advantages of high synthesis yield, good product purity, convenient operation, cheap and easily available raw materials, and suitableness for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of desvenlafaxine succinate. Background technique [0002] Desvenlafaxine succinate (Desvenlafaxinesuccinate, trade name Pristiq), chemical name RS-4-[2-dimethylamino-1-(1-hydroxycyclohexyl)ethyl]phenol succinate monohydrate ; The English name is RS-4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenolsuccinatehydrate; the molecular formula is C 16 h 25 NO 2 ·C 4 h 6 O·4H 2 O; Relative molecular weight is: 399.48; CAS registration number: 386750-22-7; Structural formula is shown in formula I: [0003] [0004] The drug is produced by Wyethphainsinc of the United States and was approved by the FDA on February 29, 2008. It is a serotonin-norepinephrine reuptake inhibitor and the main active metabolite of venlafaxine. for the treatment of major depressive disorder (MDD). [0005] Desvenlafaxine succinate is generally synthesize...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C217/70C07C213/08C07C215/64C07C51/41C07C55/10
Inventor 李龙霞黄辉胡丹丹蒋玉伟张孝清
Owner NANJING HUAWE MEDICINE TECH DEV
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