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Synthesis method of 1,4-diazaspiro[5,5]undecane hydrochloride

A diazaspiro and synthetic method technology, applied in the field of organic synthesis, can solve the problems of expensive raw materials and high cost, and achieve the effects of simple post-processing method, short synthetic route and reduced production cost

Inactive Publication Date: 2018-07-20
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to: aim at the above-mentioned existing method for synthesizing 1,4-diazaspiro[5,5]undecane hydrochloride with expensive raw materials, seriously low synthesis yield and very high cost, the present invention Provide a new synthesis method of 1,4-diazaspiro[5,5]undecane hydrochloride, the method has low raw material cost, high synthesis yield and simple post-treatment

Method used

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  • Synthesis method of 1,4-diazaspiro[5,5]undecane hydrochloride
  • Synthesis method of 1,4-diazaspiro[5,5]undecane hydrochloride
  • Synthesis method of 1,4-diazaspiro[5,5]undecane hydrochloride

Examples

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Embodiment 1

[0026] Synthesis of 1,4-diazaspiro[5,5]undecane hydrochloride:

[0027] (1) Synthesis of Compound B

[0028] Add 60mL dimethyl sulfoxide and 2mL water to a 250mL reaction flask, then add cyclohexanone (20.0g, 203.7mmol) and glycine ethyl ester hydrochloride (28.4g, 203.7mmol), fully stir to dissolve, and add cyanide in batches Sodium chloride (3.9g, 203.7mmol), stirred at room temperature for 12h until the reaction of the raw materials was complete, added 120mL of water and 120mL of methyl tert-butyl ether to the system, stirred and separated, and washed the aqueous phase with 60mL of methyl tert-butyl ether for 2- Combine the organic phases three times, wash the organic phase with water until there is no cyanide ion, and concentrate the organic phase under reduced pressure to remove methyl tert-butyl ether to obtain 34.26 g of compound B with a yield of 80%. Hydrogen peroxide or sodium hypochlorite is used to destroy the cyanide ion in the water phase, and the waste liquid i...

Embodiment 2

[0032] Synthesis of 1,4-diazaspiro[5,5]undecane hydrochloride:

[0033] (1) Synthesis of Compound B

[0034] Add 60mL dimethyl sulfoxide and 2mL water to a 250mL reaction flask, then add cyclohexanone (20.0g, 203.7mmol) and glycine ethyl ester hydrochloride (34.08g, 244.4mmol), fully stir to dissolve, and add cyanide in batches Sodium chloride (5.85g, 305.6mmol), stirred at room temperature for 12h until the reaction of the raw materials was complete, added 120mL of water and 120mL of methyl tert-butyl ether to the system, stirred and separated, and washed the aqueous phase with 60mL of methyl tert-butyl ether for 2- 3 times, the organic phase was combined, washed with water until there was no cyanide ion, and the organic phase was concentrated under reduced pressure to remove methyl tert-butyl ether to obtain 33.26 g of compound B with a yield of 74%. Hydrogen peroxide or sodium hypochlorite is used to destroy the cyanide ion in the water phase, and the waste liquid is treat...

Embodiment 3

[0038] Synthesis of 1,4-diazaspiro[5,5]undecane hydrochloride:

[0039] (1) Synthesis of Compound B

[0040] Add 60mL dimethyl sulfoxide and 2mL water into a 250mL reaction flask, then add cyclohexanone (20.0g, 203.7mmol) and glycine ethyl ester hydrochloride (34.08g, 203.7mmol), fully stir to dissolve, add cyanide in batches Sodium chloride (5.85g, 244.4mmol), stirred at room temperature for 12h until the reaction of the raw materials was complete, added 120mL of water and 120mL of methyl tert-butyl ether to the system, stirred and separated, and washed the aqueous phase with 60mL of methyl tert-butyl ether for 2- 3 times, the organic phase was combined, washed with water until there was no cyanide ion, and the organic phase was concentrated under reduced pressure to remove methyl tert-butyl ether to obtain 33.56 g of compound B with a yield of 73%. Hydrogen peroxide or sodium hypochlorite is used to destroy the cyanide ion in the water phase, and the waste liquid is treated...

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Abstract

The invention discloses 1,4-diazaspiro[5,5]undecane hydrochloride, and particularly relates to a synthesis method of 1,4-diazaspiro[5,5 undecane hydrochloride. According to the method, cheap and commercialized cyclohexanone and glycine ester are adopted as starting materials, and two-step synthesis reaction is carried out, so that compared with the prior art, the yield of the 1,4-diazaspiro[5,5]undecane hydrochloride is improved, and the overall preparation route is less in steps, simple in posttreatment and low in cost. The invention provides the brand new synthesis method of the 1,4-diazaspiro[5,5]undecane hydrochloride which is suitable for industrial scale production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 1,4-diazaspiro[5,5]undecane hydrochloride. Background technique [0002] Piperazine derivatives are important intermediates in the pharmaceutical, pesticide, and dye industries, and have a wide range of application values. Currently known methods for synthesizing 1,4-diazaspiro[5,5]undecane hydrochloride reported in the literature have the disadvantages of expensive raw materials, low synthesis yield and high cost. [0003] In the document "Journal of Medicinal Chemistry, 1995, 38, 4380-4392", the synthesis method of 1,4-diazaspiro[5,5]undecane hydrochloride is reported, and its reaction formula is: [0004] [0005] Adopt above-mentioned reaction method, product aftertreatment troublesome, need rectifying operation and the yield of last two steps is low, only 19.8%; The raw material cyclohexane formaldehyde used at the same time is expensive...

Claims

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Application Information

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IPC IPC(8): C07D241/38
CPCC07D241/38
Inventor 李楷吴黎明亢兴龙何燕郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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