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Preparation method of N-amino-3-azabicyclo[3,3,0]octane hydrochloride

A technology of hydrochloric acid and cyclopentane, applied in directions such as organic chemistry, to achieve the effect of route economy and document yield improvement

Inactive Publication Date: 2016-10-05
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] There is a step in the route disclosed in Journal of the American Chemical Society 1968 Formation of 1,1-Dianions of Hydrazones by Certain Bases. N,N-Dialkylation with Halides. Decomposition to Form Hydrocarbons involves nitrogen alkylation and condensation reaction to prepare hydrazone compounds , but the hydrazone compound is not used for the preparation of N-amino-3-azabicyclo[3,3,0]octane hydrochloride

Method used

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  • Preparation method of N-amino-3-azabicyclo[3,3,0]octane hydrochloride

Examples

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Embodiment 1

[0033]

[0034] Add 20ml of THF and 2.1g of NaH to a clean and anhydrous 100ml four-necked bottle, cool to 0-10°C under nitrogen protection, add dropwise a THF solution of 20ml of THF and 3.4g of cyclopentane-1,2-dimesylate, Control the internal temperature at 0-10°C, add 0.5h, then add 10mlTHF and 5g diphenylmethylene hydrazine dropwise in THF for 10min, heat up to reflux for 3-4h, TLC detection value raw material diphenylmethylene The hydrazine reacted completely, cooled to 20-25°C, and added 10ml of water and 50ml of ethyl acetate. The upper organic layer was separated and concentrated under reduced pressure at 40-45°C to obtain 4.5 g of the product hydrazone compound, with a yield of 90%.

[0035] 1 H NMR (400 MHz, CDCl 3 ) δ 1.391-1.2679 (m, 2H), 1.4433-1.4016 (m, 1H), 1.6704-1.5435 (m, 3H), 2.4817-2.3894 (m, 2H), 2.6676-2.6587 (dd, J= 3.6, 2H) , 2.9911-2.9717 (dd, J =2, 7.8, 2H), 7.2539-7.2456 (m, 3H), 7.3951-7.3639 (m, 5H), 7.4673-7.4620 (tt, 2H)

Embodiment 2

[0037]

[0038] Add 20ml of THF and 4.5g of hydrazone compounds into a clean and anhydrous 100ml four-neck bottle, add 10ml of 30% concentrated hydrochloric acid under stirring, and react at 40°C for 3h. TLC detects that the hydrazone compounds disappear, and reduce the reaction solution at 40-45°C. Concentrate to dryness under pressure, add 50ml of ethyl acetate and stir at 20-25°C for 0.5h, filter, collect the solid and dry to obtain 2.3g of N-amino-3-azabicyclo[3,3,0]octane hydrochloride. The yield was 90%, and 2.3 g of benzophenone was recovered from the filtrate.

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Abstract

The invention relates to a novel preparation method of N-amino-3-azabicyclo[3,3,0]octane hydrochloride. Specifically, cyclopentane-1,2-dimethanesulfonate is subjected to a reaction with a substituted hydrazine compound, such that a hydrazone compound is obtained; the hydrazone compound is subjected to a reaction with hydrochloric acid, such that the N-amino-3-azabicyclo[3,3,0]octane hydrochloride is obtained. With the reaction route, N-amino-3-azabicyclo[3,3,0]octane hydrochloride can be successfully obtained, and the other product can be recycled and used for preparing the hydrazone compound. Therefore, the route is more economical, and is suitable for industrialization.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of N-amino-3-azabicyclo[3,3,0]octane hydrochloride. Background technique [0002] N-amino-3-azabicyclo[3,3,0]octane hydrochloride is the key intermediate of gliclazide, which can be prepared by condensation with p-toluenesulfonylurea. [0003] CN101307019B (Applicant: Jiusheng Innovative Medicine, Publication Date: 2008-11-19) reported the preparation route of this intermediate, as follows: [0004] , [0005] Wherein, A and B can be mesylate groups, and n is equal to 1 or 2. [0006] Its Example 2 provides a specific route for preparing the intermediate. Add hydrazine monohydrochloride, concentrated hydrochloric acid, cis-cyclopentane-1,2-dimethylsulfonic acid, and water into the reaction flask, reflux for 4 hours, and prepare N-amino-3-aza Bicyclo[3,3,0]octane hydrochloride. [0007] Although this preparation method only needs one step, a...

Claims

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Application Information

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IPC IPC(8): C07D209/52
Inventor 朱国良陈冲杜小华
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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