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Chemical synthesis process of 1-chloroformyl-4-piperidyl hydrochloride

A technology of piperidinylpiperidine and chloroformyl, which is applied in the field of chemical synthesis of 1-chloroformyl-4-piperidinylpiperidine hydrochloride, which can solve the problems of heavy pollution, equipment corrosion, and difficulty in the treatment of three wastes, etc. problems, achieve the effects of less waste, low production cost, and mild reaction conditions

Active Publication Date: 2009-06-03
浙江遂昌利民科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, phosphorus trichloride or thionyl chloride are also traditional chlorination reagents, which are widely used in organic synthesis, but phosphorus trichloride or thionyl chloride are corrosive substances, which are used for equipment corrosion in production. Serious, heavy pollution, difficult to treat the three wastes

Method used

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  • Chemical synthesis process of 1-chloroformyl-4-piperidyl hydrochloride
  • Chemical synthesis process of 1-chloroformyl-4-piperidyl hydrochloride
  • Chemical synthesis process of 1-chloroformyl-4-piperidyl hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0034] The feed ratio of 4-piperidinylpiperidine:bis(trichloromethyl)carbonate is 1:0.40 (molar ratio), and tetrahydrofuran is used as an organic solvent, and its dosage is 8 times the mass of 4-piperidinylpiperidine.

[0035] In a four-necked flask equipped with mechanical stirring, reflux condenser, thermometer and constant pressure titration funnel, add bis(trichloromethyl) carbonate (5.9g, 20mmol) and tetrahydrofuran (50mL), turn on mechanical stirring until the solution is clear . A solution of 4-piperidinylpiperidine (8.4g, 50mmol) in tetrahydrofuran (17mL) was slowly added dropwise at about 10°C. The mixture was stirred for 0.5h while keeping warm. The oil bath was heated to reflux temperature, and the reflux time was 2h. After the reaction is completed, cool to room temperature, filter, recover a small amount of filter cake, concentrate the filtrate, add the washing solvent cyclohexane, the volume consumption (mL) is 5 times the crude quality (g), white solid precipitates,...

Embodiment 2

[0038] Feeding ratio 4-piperidylpiperidine: bis(trichloromethyl)carbonate is 1:0.46 (molar ratio), 4-piperidylpiperidine feeding amount is 50mmol, bis(trichloromethyl)carbonate feeding The amount is 23 mmol, and tetrahydrofuran is used as an organic solvent, and the amount is 8 times the mass of 4-piperidinylpiperidine. The volume consumption (mL) of the washing solvent cyclohexane is 5 times of the crude quality (g).

[0039] Other operations are the same as in Example 1, the product yield is 81.8%, and the purity is 98.0%.

Embodiment 3

[0041] Feeding ratio 4-piperidinylpiperidine: bis(trichloromethyl) carbonate is 1:0.44 (molar ratio), 4-piperidylpiperidine feeding amount is 50mmol, bis(trichloromethyl) carbonate feeding The amount is 22 mmol, and tetrahydrofuran is used as an organic solvent, and the amount is 8 times the mass of 4-piperidinylpiperidine. The volume consumption (mL) of the washing solvent cyclohexane is 5 times of the crude quality (g).

[0042] Other operations are the same as in Example 1. The product yield is 80.5% and purity is 99.2%. ( 1 H NMR(δ): 4.52(2H, d, J=10.8, CH 2 ), 2.47(3H, s, CH or CH 2), 3.18 (1H, s, CH), 2.96 (1H, s, CH), 2.76 (2H, s, CH) 2 ), 2.47 (4H, s, CH 2 ), 1.97-1.82(5H, m, CH or CH 2 ), 1.40(2H, d, J=12.0, CH 2 ); 13 C NMR (δ): 148.13, 63.12, 50.20, 49.61, 47.22, 44.53, 26.16, 25.33, 22.68, 22.36; MS: 230, 232; IR (cm -1 ))): 1715.65 (C=O)).

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Abstract

The present invention relates to process of preparing 1-chloroformyl-4-piperidyl hydrochloride with bis (trichloromethyl) carbonate to replace phosgene, diphosgene, chloro sulfoxide and other virulent and harmful material. The process of the present invention has high yield, high product purity, no need of catalyst, low production cost, less environmental pollution and other advantages.

Description

(1) Technical field [0001] The present invention relates to a preparation of 1-chloroformyl by using bis(trichloromethyl) carbonate to replace phosgene, diphosgene, thionyl chloride, phosphorus trichloride, phosphorus pentachloride and other highly toxic and harmful substances The chemical method of 4-piperidinylpiperidine hydrochloride. This product is a key intermediate of the anti-tumor drug irinotecan and has high practical value. (2) Background technology [0002] Before the present invention was made, the prior art chemical synthesis method of 1-chloroformyl-4-piperidinylpiperidine hydrochloride used phosgene or diphosgene as the chlorinating reagent, such as 4-piperidine as proposed in JP 2002371061 The pyridylpiperidine reacted with phosgene in tetrahydrofuran at 5℃ for 1 hour, and then suspended in n-hexane with K 2 CO 3 70% of 1-chloroformyl-4-piperidinylpiperidine can be obtained by processing; or using trimethylchlorosilane as a catalyst, the reaction of carbon dioxid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/60
Inventor 梁现蕊苏为科李峰濮发祥赖晓春张建萍
Owner 浙江遂昌利民科技有限公司