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Method for synthesis of alpha,alpha-diphenyl-4-piperidine methanol

A technology of piperidinemethanol and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high production cost, and achieve the effects of low production cost, suitable for industrialization, and easy operation

Inactive Publication Date: 2014-08-27
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to solve the above-mentioned technical problem of high production cost of α, α-diphenyl-4-piperidinemethanol, and provide a kind of α,α-diphenyl-4-piperidinemethanol with low production cost Synthetic method, the method has the characteristics of easy operation and suitable for industrial synthesis of α,α-diphenyl-4-piperidinemethanol

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  • Method for synthesis of alpha,alpha-diphenyl-4-piperidine methanol

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Embodiment 1

[0030] A kind of α, the synthetic method of α-diphenyl-4-piperidinemethanol, the concrete steps of its synthetic process are as follows:

[0031] (1) Synthesis of N-acetyl-4-piperidinecarboxylic acid

[0032] Add 4-piperidinecarboxylic acid (38.8g, 0.30mol) and 58mL of acetic anhydride to a 250 mL four-necked flask equipped with a drying tube at the mouth of the condenser, slowly raise the temperature to reflux and continue for 6 hours, TLC detects that the reaction is complete, and the obtained The reaction solution was cooled to room temperature, a large amount of light brown solids were precipitated, the solids were filtered out with suction, and the solids were washed with an appropriate amount of methyl tert-butyl ether and then filtered with suction to obtain light brown solids, which were recrystallized with methanol to obtain 46.3 g of off-white solids. Yield 90.1%;

[0033] The amount of 4-piperidinecarboxylic acid and acetylating reagent used in the above N-acetylat...

Embodiment 2

[0050] A kind of α, the synthetic method of α-diphenyl-4-piperidinemethanol, the concrete steps of its synthetic process are as follows:

[0051] (1) Add 4-piperidinecarboxylic acid (38.8g, 0.30mol) and 32 mL of acetyl chloride into a 250 mL four-necked flask equipped with a drying tube at the mouth of the condenser, slowly raise the temperature to reflux and continue for 4 hours, TLC After the detection reaction was completed, the resulting reaction liquid was cooled to room temperature, and a large amount of light brown solids were precipitated, and the solids were filtered out with suction. The solids were washed with an appropriate amount of methyl tert-butyl ether and then filtered with suction to obtain a light brown solid, which was recrystallized with methanol to obtain a White solid 46.3g, yield 90.1%;

[0052] The amount of 4-piperidinecarboxylic acid and acetylating reagent used in the above N-acetylation reaction is calculated in molar ratio, that is, 4-piperidinec...

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Abstract

The invention discloses a method for synthesis of alpha,alpha-diphenyl-4-piperidine methanol. The method comprises the steps: taking 4-piperidine formic acid as a raw material, carrying out a reaction with an acetylation reagent to obtain N-acetyl piperidine formic acid; firstly generating N-acetyl piperidine formyl chloride from the obtained N-acetyl piperidine formic acid, and then carrying out a Friedel-Crafts acylation reaction with benzene to generate N-acetyl-4-benzoyl piperidine; carrying out a Grignard reaction of the obtained N-acetyl-4-benzoyl piperidine with phenyl magnesium halide to obtain N-acetyl-alpha,alpha-diphenyl-4-piperidine methanol; and deacetylating the N-acetyl-alpha,alpha-diphenyl-4-piperidine methanol to obtain the alpha,alpha-diphenyl-4-piperidine methanol. The synthesis method has the characteristics of cheap and easily obtained raw materials, simple process steps, high reaction yield and low costs of raw materials, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing α,α-diphenyl-4-piperidinemethanol. Specifically, 4-piperidinecarboxylic acid is used as a raw material to obtain α,α-diphenyl-4-piperidine through N-acetylation, Friedel-Crafts acylation, addition of Grignard reagent phenylmagnesium halide, and hydrolysis to deacetylate pyridinemethanol. It belongs to the field of organic chemical synthesis. Background technique [0002] α,α-Diphenyl-4-piperidinemethanol, also known as Azacyclonol, is a key intermediate in the synthesis of antihistamines such as fexofenadine hydrochloride. α,α-Diphenyl-4-piperidinemethanol has been traditionally synthesized by three routes: the first one uses α,α-diphenyl-4-pyridinemethanol as raw material, and undergoes high-pressure reduction with Pt / C and hydrogen The second route is to use 4-cyanopyridine as raw material to generate sodium salt with metal sodium, and then couple with benzophenone through free radical coupling an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22
CPCC07D211/22
Inventor 肖繁花吴范宏
Owner SHANGHAI INST OF TECH
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