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A method for preparing 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine

A technology of tert-butoxycarbonyl and pyridyl, which is applied in the field of organic chemical preparation and can solve problems such as piperazine compounds.

Active Publication Date: 2022-06-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the reductive alkylation of simple aromatic nitro compounds has been reported in the literature, this type of reaction has not been used for 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl] Report on the Preparation of Piperazine Compounds

Method used

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  • A method for preparing 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine
  • A method for preparing 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine
  • A method for preparing 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 1-tert-butoxycarbonyl-4-(3-isopropylamino-2-pyridyl)piperazine

[0024]

[0025] a. 10.0 g (32 mmol) of 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl) piperazine, catalyst Pd-C (Pd content 10%, mass percent) 1.0 g, cocatalyst 0.5 g of p-toluenesulfonic acid and 9.5 g (163 mmol) of acetone were mixed and added to a stainless steel autoclave.

[0026] b. At room temperature, replace the air with nitrogen for 3 times, hydrogen in the kettle for 3 times, and replace the pressure in the kettle with 0.1MPa.

[0027] c. Stir the reactant at 50°C, feed hydrogen, and the pressure in the kettle is 2.0MPa, and react until liquid chromatography detects raw materials 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl)piperazine and The remaining mass percentage of the intermediate 1-tert-butoxycarbonyl-4-(3-amino-2-pyridyl)piperazine is less than 1%, and the reaction is stopped.

[0028] d. The reaction system was lowered to room temperature, filtered, the catalyst was recycled,...

Embodiment 2

[0030] Example 2 1-tert-butoxycarbonyl-4-(3-isopropylamino-2-pyridyl)piperazine

[0031]

[0032] a. 10.0g (32mmol) of 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl)piperazine, catalyst Pt-C (10%, mass percent) 1.0g, cocatalyst p-toluenesulfonate Mix 0.5 g of acid and 9.5 g (163 mmol) of acetone, and add to a stainless steel autoclave.

[0033] b. At room temperature, replace the air with nitrogen for 3 times, hydrogen in the kettle for 3 times, and replace the pressure in the kettle with 0.1MPa.

[0034] c. Stir at 50°C, feed hydrogen, pressure 2.0MPa, react until liquid chromatography detects raw material 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl)piperazine and intermediate 1- The remaining mass percentage of tert-butoxycarbonyl-4-(3-amino-2-pyridyl)piperazine is less than 1%, and the reaction is stopped.

[0035] d. The reaction system was lowered to room temperature, filtered, the catalyst was recycled, the liquid was separated to remove the lower aqueous layer, the upp...

Embodiment 3

[0037] Example 3 1-tert-butoxycarbonyl-4-(3-isopropylamino-2-pyridyl)piperazine

[0038]

[0039] a. 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl)piperazine 10.0g (32mmol), catalyst Pt-C (10%, mass percent) 0.5g, Pd-C (10 %, mass percent) 0.5g, cocatalyst p-toluenesulfonic acid 0.5g, acetone 9.5g (163mmol) are mixed, add in the stainless steel autoclave.

[0040] b. At room temperature, replace the air with nitrogen for 3 times, hydrogen in the kettle for 3 times, and replace the pressure in the kettle with 0.1MPa.

[0041] c. Stir at 50°C, feed hydrogen, and the pressure in the kettle is 4.0MPa, react until liquid chromatography detects the raw material 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl)piperazine and intermediates The remaining mass percentage of 1-tert-butoxycarbonyl-4-(3-amino-2-pyridyl)piperazine is less than 1%, and the reaction is stopped.

[0042] d. The reaction system was lowered to room temperature, filtered, the catalyst was recycled, the liquid was separ...

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Abstract

The invention discloses a method for preparing 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine, which belongs to the technical field of organic chemical preparation. The present invention mixes 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl) piperazine, a catalyst, a cocatalyst and an alkyl ketone, and adds them into a pressure-resistant kettle; Air in the autoclave, and then continue to feed hydrogen to react; the reaction system was lowered to room temperature, filtered, and the lower water layer was separated, the upper organic layer was dried, filtered to remove the desiccant, concentrated by distillation, and recrystallized to obtain the target product. The present invention uses 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl)piperazine as a starting material, and carries out a reductive alkylation reaction under the conditions of the presence of alkyl ketones, catalysts and hydrogen. Preparation of 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine in one reactor. The method has the characteristics of simple operation and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic chemical preparation, and in particular relates to a method for preparing 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine. Background technique [0002] 1-tert-butoxycarbonyl-4-[3-(alkylamino)-2-pyridyl]piperazine is a class of organic compounds with special biological activity and is an important intermediate for the preparation of the anti-AIDS drug delavirdine. There are two reports on the preparation method of this intermediate in the literature, and the patent WO 2011103559 reports the preparation by reductive alkylation of 1-tert-butoxycarbonyl-4-[3-amino-2-pyridyl]piperazine and acetone The method of this compound, Chinese Journal of Pharmaceutical Industry (42,648-650; 2011) reported the use of 1-tert-butoxycarbonyl-4-[3-nitro-2-pyridyl]piperazine through reduction, imidization, reduction, etc. A multi-step reaction to prepare the compound. These preparation methods are char...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/75
Inventor 郑良玉张锁秦
Owner JILIN UNIV
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