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Method for preparing sertindole

A technology of sertindole and compounds, which is applied in the direction of pharmaceutical formulas, medical preparations containing active ingredients, cardiovascular system diseases, etc., can solve the problems of high synthesis cost and many reaction steps, and achieve simplified reaction steps and high reaction yield High, beneficial to the effect of industrial production

Inactive Publication Date: 2009-02-11
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The purpose of the present invention is to disclose a preparation method of sertindole, so as to overcome the defects of many reaction steps and high synthesis cost in the prior art

Method used

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  • Method for preparing sertindole
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  • Method for preparing sertindole

Examples

Experimental program
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Embodiment 1

[0036] Synthesis of (2-chloroethylimidazoline)-2-one (8)

[0037] Put N-(2-hydroxyethyl)ethylenediamine compound (15) (104g, 1mol) and urea (60.06g, 1mol) in a 500ml single-necked bottle, react at 230°C for 4h, and the reaction is complete. Cool, wash 3 times with ether (×150ml), filter, and dissolve the filter cake in 300mlCH 2 Cl 2 In ice bath, slowly add SOCl dropwise 2 (86ml), dropwise, heated to reflux for 3h, quenched the reaction with dilute alkaline water, extracted and separated, the aqueous layer was backwashed with dichloromethane (100ml), the dichloromethane layers were combined, evaporated to dryness, and the resulting solid was diethyl ether ( 80ml) was washed to obtain (2-chloroethylimidazoline)-2-one as light yellow solid 117.80g, and the two-step yield was 79.3%. m.p.86.0~86.4℃. MS (m / z): 149.1 (M+H).

Embodiment 2

[0039] Synthesis of 1-(2-(2-carbonylimidazoline)ethyl)piperidin-4-one (13)

[0040] The raw material (2-chloroethylimidazoline)-2-ketone (19g, 0.128mol), piperidone hydrochloride monohydrate (12) (14g, 0.091mol), NaHCO 3 (23g, 0.273mol) was placed in 120ml of methyl isobutyl ketone, reacted for 24 hours at 95-100°C, filtered, evaporated to dryness, and the product obtained was washed with tetrahydrofuran to obtain 14.09g of the product, with a yield of 63.44%. m.p.115-118°C, MS (m / z): 212.1 (M+H). 1 HNMR (400MHz, CDCl 3 )δ: 2.41(t, 4H), 2.61(t, 2H), 2.78(t, 4H), 3.32(t, 2H), 3.36~3.38(m, 2H), 3.47~3.51(m, 2H), 5.11 (s, 1H).

Embodiment 3

[0042] (2-chloroethylimidazoline)-2-ketone (30g, 0.202mol), piperidone hydrochloride monohydrate (22g, 0.144mol) and NaHCO 3 (36g, 0.432mol) was placed in 200ml MIBK, and reacted at 80°C for 30 hours to obtain 15.3g of compound (13), with a yield of 50.3%. Melting point and spectral data are the same as above.

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Abstract

The invention discloses a preparation method of sertindole, which comprises the following steps: a compound with chemical constitution shown as (5) and a compound with chemical constitution shown as (13) react to obtain a compound with chemical constitution shown as (9) and then the target product of sertindole (I) is prepared. The invention adopts the method to prepare sertindole, which has the following advantages: key intermediate 1-(4-fluorophenyl)-5-chlorine indole (5) and 1-(2-(2-carbonyl imidazoline) ethyl) piperidine-4-ketone (13) are condensed to directly obtain an intermediate applied to preparing the sertindole, thus shortening reaction line, leading to high reaction yield, simplifying reaction steps, reducing cost and being more conducive to industrialized production. The reaction general formula is shown as the above formula.

Description

technical field [0001] The invention relates to a method for synthesizing sertindole. Background technique [0002] Sertindole is an atypical antipsychotic drug, its English name is Sertindole, its trade name is Serdolect (Serlect), and its chemical name is: 1-[2-[4-[5-chloro-1-(4-fluorophenyl)- 1H-indol-3-yl]-1-piperidinyl]ethyl-2-imidazolidinone. The English name is: 5-Chloro-1-(4-fluorophenyl)-3-[1-(2-oxoimidazolidin-1-ylethyl)-4-piperidyl]-1H-indole; or 1-[2-[4-[ 5-Chloro-1-(4-fluorophenyl)-1H-indol-3-y1]piperidinyl]ethyl]-2-imidazolidinone. The chemical structural formula of sertindole is shown in (I): [0003] [0004] This compound is disclosed in US 4,710,500 and its antischizophrenic activity is disclosed in US 5,112,838. In vivo, sertindole acts on the central nervous system D 2 and 5-HT 2A Antagonist of the receptor, and has further shown therapeutic effects in models of anxiety, hypertension, drug abuse and cognitive impairment. [0005] The synthetic r...

Claims

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Application Information

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IPC IPC(8): C07D401/14A61K31/454A61P25/22A61P25/28A61P9/12A61P25/30
Inventor 李建其叶雪雁黄丽瑛彭少平
Owner SHANGHAI INST OF PHARMA IND
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