Preparation method of pyrrolizidine-9-acetic acid hydrochloride

A technology of double-condensed pyrrolidine chlorate and double-condensed pyrrolidine, which is applied in the field of preparation of double-condensed pyrrolidine-9-acetic acid hydrochloride, can solve the problem that the preparation method and extraction amount of double-condensed pyrrolidine are not given. Less, complex process and other problems, to achieve the effect of simplifying the preparation process, optimizing the reaction temperature, and improving the reaction yield

Inactive Publication Date: 2010-12-15
苏州永拓医药科技有限公司
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  • Application Information

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Problems solved by technology

[0005] The Chinese patent "Preparation Method of Pyrrolazine Derivatives" (publication number: CN1038452A) discloses a method for preparing 7α-cyano group by reacting 1,7 dichloro-4-heptanone with ammonia, acetone cyanohydrin and NaOH -A method for 2,3,5,6,7α-hexahydro-pyrrolazine, b

Method used

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  • Preparation method of pyrrolizidine-9-acetic acid hydrochloride
  • Preparation method of pyrrolizidine-9-acetic acid hydrochloride
  • Preparation method of pyrrolizidine-9-acetic acid hydrochloride

Examples

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preparation example Construction

[0047] Step 1) preparation of double-condensed pyrrolidine chlorate;

[0048] Step 2) preparation of double-condensed pyrrolidine-9-acetocyanide;

[0049] Step 3) Preparation of double-condensed pyrrolidine-9-acetic acid hydrochloride.

Embodiment 1

[0051] (1) Preparation of double-condensed pyrrolidinium chlorate

[0052] According to the method disclosed in the former Soviet Union Patent SU1351919A, 1,7-di-p-nitrobenzenesulfonate-4-heptanone was prepared.

[0053] Connect a 2000ml four-necked explosion-proof reaction flask with a low-temperature cooling circulation device and a thermometer. Add 675ml of concentrated ammonia water and 240g of ammonium chloride to the reaction flask, use a low-temperature cooling device to cool the temperature of the reaction solution to -10°C, then add 536g of 1,7-di-p-nitrobenzenesulfonate-4-heptanone, and pass Add ammonia gas, increase the pressure in the container to 6-8MPa, control the reaction temperature at 5-10°C, and react for 15 hours.

[0054] After the reaction, the reaction solution was spin-dried, and the solid was washed with 500ml of dichloromethane (DCM), filtered with suction, and the mother liquor was spin-dried to obtain 125g of a light yellow crude product, which was...

Embodiment 2-4

[0060] Embodiment 2-4 is to illustrate the yield of double-condensed pyrrolidinium chlorate during different charging ratios, and other implementation steps are referring to embodiment 1.

[0061] According to the steps described in Example 1, double-condensed pyrrolidinium chlorate is prepared, wherein 1,7-di-p-nitrobenzenesulfonate-4-heptanone and the feeding amount of concentrated ammonia water and the corresponding product amount and yield respectively As shown in Table 1.

[0062] Product amount and yield table of double condensed pyrrolidinium chlorate of table 1

[0063] Example

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Abstract

The invention discloses a preparation method of pyrrolizidine-9-acetic acid hydrochloride, comprising the following chemical reactions: 1) preparing 1,7-bi-p-nitryl benzenesulfonate -4-heptanone as a raw material according to the prior art for reacting with ammonium chloride and ammonia to generate pyrrolizidine-chlorate; 2) reacting the pyrrolizidine-chlorate with sodium cyanoacetate to generate pyrrolizidine-9-acetonitrile; and 3) allowing the pyrrolizidine-9-acetonitrile with concentrated hydrochloric acid to generate the pyrrolizidine-9-acetic acid hydrochloride. By adopting a chemical synthesis method, the preparation method of the invention greatly simplifies preparation flow, shortens reaction time and effectively lowers production cost; and the pyrrolizidine-9-acetic acid hydrochloride prepared by the preparation method has high yield and good quality, thus meeting the need of industrialized production.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of double-condensed pyrrolidine-9-acetic acid hydrochloride. Background technique [0002] The double-condensed pyrrolidine-9-acetic acid hydrochloride is an intermediate of the heart disease drug Pisicarib, and the chemical structure of the double-condensed pyrrolidine-9-acetic acid hydrochloride is shown in formula (I). [0003] [0004] Pisicarib [N-(2,6-dimethylphenyl)-8-dicondensed pyrrole-acetamide hydrochloride hemihydrate] is an orally effective class Ic antiarrhythmic drug for ventricular Or supraventricular arrhythmia, especially for the treatment of ventricular tachycardia that other antiarrhythmic drugs are ineffective or intolerable, and rarely cause central nervous system adverse reactions and anticholinergic effects. Pisicarib has the following pharmacokinetic characteristics: fast absorption from the gastrointestinal tract, no hepatic firs...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 金柏峰周永达王俊
Owner 苏州永拓医药科技有限公司
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