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Preparation method of 1-(2-pyrimidine) piperazine hydrochloride

A technology of hydrochloride and piperazine, applied in the field of medicinal chemistry, can solve the problems of affecting the yield and purity of the product, increasing the difficulty of storage, darkening the color of the product, etc., and achieving suitable for industrial production, easy operation and mild reaction conditions. Effect

Active Publication Date: 2015-07-29
NHWA PHARMA CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The current synthesis is mainly prepared by the condensation reaction of 2-chloropyrimidine and piperazine under alkaline conditions. The reaction uses dichloromethane, chloroform, etc. as solvents. During the reaction, a large number of by-products are produced, which seriously affects the product. High yield and purity, high production cost
At the same time, piperazine pyrimidine is a liquid viscous substance, which will be oxidized by oxygen in the air when it is placed, making the color of the product darker and increasing the difficulty of storage

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the preparation of 1-(2-pyrimidine)-4-Boc piperazine

[0016] At 25°C, toward Na 2 CO 3 (21.2g, 0.22mol) in water (300mL) was added Boc-piperazine (37.2g, 0.2mol). 2-Chloropyrimidine (25.2 g, 0.22 mol) was added portionwise with stirring, then stirring was continued at this temperature for 3 h. After filtering, the filter cake was washed twice with a small amount of water, and dried to obtain a white powdery solid, namely 1-(2-pyrimidine)-4-Boc piperazine (49.2 g, 93.1%), with a content of 99.5%. [ 1 H NMR (400MHz, CDCl 3 )δ8.32(t,J=7.4Hz,2H),6.50(t,J=4.7Hz,1H),3.87–3.74(m,4H),3.55–3.43(m,4H),1.47(d,J =9.9Hz,9H).]

Embodiment 2

[0017] Embodiment 2: Preparation of 1-(2-pyrimidine)-4-Boc piperazine

[0018] 25°C, toward K 2 CO 3 (30.4g, 0.22mol) in water (300mL) was added Boc-piperazine (37.2g, 0.2mol). 2-Chloropyrimidine (25.2 g, 0.22 mol) was added portionwise with stirring, then stirring was continued at this temperature for 3 h. After filtering, the filter cake was washed twice with a small amount of water, and dried to obtain a white powdery solid, namely 1-(2-pyrimidine)-4-Boc piperazine (48.3 g, 91.4%), with a content of 99.2%.

Embodiment 3

[0019] Embodiment 3: the preparation of 1-(2-pyrimidine)-4-Boc piperazine

[0020] At 25°C, to (NH 4 ) 2 CO 3 (21.1 g, 0.22 mol) in water (300 mL) was added Boc-piperazine (37.2 g, 0.2 mol). 2-Chloropyrimidine (25.2 g, 0.22 mol) was added portionwise with stirring, then stirring was continued at this temperature for 3 h. After filtering, the filter cake was washed twice with a small amount of water, and dried to obtain a white powdery solid, namely 1-(2-pyrimidine)-4-Boc piperazine (47.3 g, 89.6%), with a content of 98.7%.

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Abstract

The invention discloses a novel method for preparing 1-(2-pyrimidine) piperazine hydrochloride. The method comprises the following steps: under alkaline conditions, enabling N-Boc-piperazine and 2-chloro-pyrimidine to be subjected to condensation reaction to obtain 1-(2-pyrimidine)-4-Boc-piperazine and then hydrolyzing under acidic conditions to obtain the 1-(2-pyrimidine) piperazine hydrochloride. The 1-(2-pyrimidine) piperazine hydrochloride prepared by the novel method is simple in reaction process, less in impurity, convenient for storage, low in cost and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a preparation method of 1-(2-pyrimidine)piperazine hydrochloride. Background technique [0002] 1-(2-pyrimidine) piperazine, referred to as piperazine pyrimidine, is an intermediate for the synthesis of the new anxiolytic drug buspirone. The current synthesis is mainly prepared by the condensation reaction of 2-chloropyrimidine and piperazine under alkaline conditions. The reaction uses dichloromethane, chloroform, etc. as solvents. During the reaction, a large number of by-products are produced, which seriously affects the product. The yield and purity are high, and the production cost is high. At the same time, piperazine pyrimidine is a liquid viscous substance, which will be oxidized by oxygen in the air when placed, making the product darker and making storage more difficult. [0003] Based on the limitations of the above synthetic methods of piperazine pyrimidine, it is ne...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 安顺永俞文才王玲伟
Owner NHWA PHARMA CORPORATION
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