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Method for preparing quaternary ammonium salt containing adamantine alkyl

A technology of adamantane trimethylammonium halide salt and adamantyl, which is applied in the field of preparation of quaternary ammonium salts with adamantyl, and can solve the problems of incomplete reaction of raw materials, impossibility of purification, impossibility of improving purity, etc.

Inactive Publication Date: 2011-01-05
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, when using this synthesis method, tributylmethylamine iodide salt is generated, and the purity cannot be improved.
[0008] In addition, in Non-Patent Document 1, a method of synthesizing a quaternary ammonium halide salt using methyl halide through dimethylation of aminoadamantane is described, but it is difficult to use this synthesis method industrially due to the long reaction time. , due to the incomplete reaction of the raw material and the impossibility of purification, the target object cannot be obtained with high purity and high yield

Method used

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  • Method for preparing quaternary ammonium salt containing adamantine alkyl
  • Method for preparing quaternary ammonium salt containing adamantine alkyl
  • Method for preparing quaternary ammonium salt containing adamantine alkyl

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[0052] The preparation method of the quaternary ammonium salt having an adamantyl group of the present invention is characterized in that step A and step B are included in sequence.

[0053] [Step A]

[0054] Step A is a step selected from the steps shown in the following reaction formula, including a manufacturing step selected from the following steps: when using amantadine hydrochloride [following formula (1-1)] as the starting material, dissolving in Relative permittivity is the reactant of bases such as amantadine hydrochloride and alkali metal hydroxide in the solvent a of 10.0~20.0 reacts with formic acid and formaldehyde or paraformaldehyde, forms 1-adamantane dimethylamine [following formula (2 )], or when using 1-aminoadamantane [following formula (1-2)] as a starting material, the 1-aminoadamantane dissolved in solvent a reacts with formic acid and formaldehyde or paraformaldehyde to form The step of 1-adamantane dimethylamine [following formula (2)], and then when...

Embodiment 1

[0142] Add 39.4 g of amantadine hydrochloride [FW: 187.11, 0.21 mol] and 200 mL of 2-propanol (relative dielectric constant: 18) into a 500 ml three-necked flask equipped with a reflux condenser, a thermometer, and a stirrer to dissolve. After raising the temperature of the solution to 50°C, 17 g of a 50% by mass aqueous sodium hydroxide solution was slowly added dropwise, stirred for 1 hour, and then 30 ml of a 97% by mass formic acid aqueous solution [FW: 46.03, 0.77 mol] was slowly added dropwise. While stirring, 85 g [FW: 30.03, 1.05 mol] of 37 mass % formaldehyde aqueous solution was dripped over 30 minutes. After completion of the dropwise addition, the temperature was raised to 80° C., and the reaction was performed for 3 hours. The reaction liquid was cooled, and it adjusted to pH 10 using 25 mass % sodium hydroxide aqueous solution. Add 250 ml of ethyl acetate, and separate the organic phase.

[0143] Add the fractionated crude 1-adamantyldimethylamine solution into...

Embodiment 2

[0145] 39.4 g of amantadine hydrochloride [FW: 187.11, 0.21 mol] and 200 mL of 2-propanol were added to a 500 ml three-necked flask equipped with a reflux condenser, a thermometer, and a stirrer, and dissolved. After raising the temperature of the solution to 50°C, 17 g of a 50% by mass aqueous sodium hydroxide solution was slowly added dropwise, stirred for 1 hour, and then 30 ml of a 97% by mass formic acid aqueous solution [FW: 46.03, 0.77 mol] was slowly added dropwise. While stirring, 85 g [FW: 30.03, 1.05 mol] of 37 mass % formaldehyde aqueous solution was dripped over 30 minutes. After completion of the dropwise addition, the temperature was raised to 80° C., and the reaction was performed for 3 hours. The reaction liquid was cooled, and it adjusted to pH 10 using 25 mass % sodium hydroxide aqueous solution. Add 250 ml of ethyl acetate, and separate the organic phase.

[0146] Add the fractionated crude 1-adamantyldimethylamine solution into a 500ml three-necked flask...

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Abstract

The present invention relates to a method for preparing a quaternary ammonium salt containing adamantine alkyl. By means of the method of the invention, it is possible to effectively in a short time and industrially high-yield and high -purity prepare the quaternary ammonium salt containing the adamantine alkyl. The method is characterized in that it includes a step A and a step B, step A: a step of preparing 1-adamantane dimethyl amine (formula (2)) selected from a step of reacting a reactant of an adamantane hydrochloric acid and a base metal hydroxide dissolved in a solvent (a) which relative inductivity is 10.0 to 20.0 with aminic acid and methyl aldehyde or paraformaldehyde, a step of reacting 1-amidogen adamantane dissolved in the solvent (a) with aminic acid and methyl aldehyde or paraformaldehyde, and a step of reacting 1-halogeno adamantane with dimethyl amine; step B: a step of preparing a 1-adamantane trimethyl halogenation aminium salt by reacting the 1-adamantane dimethyl amine of the step A dissolved in a solvent (b) with halomethane.

Description

technical field [0001] The present invention relates to the preparation method of the quaternary ammonium salt with adamantyl group, more specifically, relates to the method for preparing the quaternary ammonium salt with adamantyl group with high yield and high purity. Background technique [0002] Adamantane has a structure of four cyclohexane rings condensed into a cage shape. It is a stable compound with high symmetry. Its derivatives show specific functions. Therefore, it is known that it is a raw material for pharmaceuticals and high-functional industrial materials. useful. [0003] For example, adamantane derivatives have been tried to be used in optical disk substrates, optical fibers, lenses, etc. due to their optical properties, heat resistance, etc. (see, for example, Patent Documents 1 and 2). [0004] In addition, adamantyl esters have been attempted to be used as resin raw materials for photoresists by utilizing their acid sensitivity, dry etching resistance, ...

Claims

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Application Information

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IPC IPC(8): C07C211/63C07C211/38C07C209/12C07C209/68
Inventor 伊藤克树河野直弥小岛明雄大野英俊
Owner IDEMITSU KOSAN CO LTD
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