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Preparation method of 2-methylethylamine

A technology of methylethylamine and methoxyethylamine, applied in the field of preparation of 2-methylethylamine, can solve the problems of uneconomical atoms, uncontrollable generation of secondary amines and even tertiary amines, etc., and achieves convenient quality. Control, good application prospects, avoid the effect of the use of highly toxic methylating reagents

Pending Publication Date: 2022-02-01
SUZHOU HIGHFINE BIOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Two) In addition, there are many reports on the method of utilizing ruthenium (Ru) metal ligands to catalyze the synthesis of 2-methoxyethylamine
[0015] 5) In addition, the synthesis of 2-methoxyethylamine by the reaction of ammonia and methoxybromoethane has also been reported, but this method cannot control the formation of secondary amines or even tertiary amines (Tetrahedron letters2004,45,397-399)
However, this synthetic route is very uneconomical

Method used

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  • Preparation method of 2-methylethylamine
  • Preparation method of 2-methylethylamine
  • Preparation method of 2-methylethylamine

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[0039] The preparation method of 2-methylethylamine according to the embodiment of the present invention comprises the following steps:

[0040] Step S1, using 2-bromoethylamine hydrobromide as a starting material, performing Boc protection on the ethylamine group in 2-bromoethylamine hydrobromide to obtain N-Boc bromoethylamine.

[0041] That is to say, the preparation method of the present invention uses 2-bromoethylamine hydrobromide as a starting material. First, the ethylamine group in the starting material is Boc-protected to obtain intermediate 1, namely N-Boc bromoethylamine.

[0042] The reaction formula is shown in the following formula (8).

[0043]

[0044] Further, in the step S1, the ethylamine group in the 2-bromoethylamine hydrobromide is Boc-protected by Boc anhydride in the first solvent in the presence of a base.

[0045] Furthermore, the first solvent is one or more of dichloromethane, 1,2-dichloroethane, tetrahydrofuran, and ethyl acetate. The starti...

Embodiment 1

[0070] (1) Preparation of N-Boc bromoethylamine

[0071] Add 2-bromoethylamine hydrobromide (800g, 3.9mol) and methylene dichloride in the 10L three-necked flask, control system temperature and drip triethylamine (1261.4g, 9.76mol) successively within room temperature, then control temperature at 10 Below ℃, BOC anhydride (894.8 g, 4.1 mol) was added dropwise, and after the drop was completed, it was naturally raised to room temperature to continue the reaction for 5 hours. Add water to the reaction liquid and stir to separate the liquids. After acid washing with dichloromethane, dry, filter and concentrate, the crude product is pulped with petroleum ether, and 708 g of white solid is obtained from the crude product, which is directly used in the next step without purification.

[0072] (2) Preparation of N-Boc-2-methoxyethylamine

[0073] Add the N-Boc bromoethylamine (700g) and methanol obtained above into a 10L three-necked flask, control the temperature of the system belo...

Embodiment 2

[0083] (1) Preparation of N-Boc bromoethylamine

[0084] Add 2-bromoethylamine hydrobromide (800g, 3.9mol) and dichloromethane in the 10L three-necked flask, control system temperature and drip diisopropylethylamine (987.7g, 9.76mol) successively within room temperature, then control BOC anhydride (894.8 g, 4.1 mol) was added dropwise at a temperature below 10° C. After the drop was completed, it was naturally raised to room temperature to continue the reaction for 5 hours. Add water to the reaction solution and stir to separate the liquids. After acid washing with dichloromethane, dry, filter and concentrate, the crude product is pulped with petroleum ether, and 700 g of white solid is obtained from the crude product, which is directly used in the next step without purification.

[0085] (2) Preparation of N-Boc-2-methoxyethylamine

[0086] Add the N-Boc bromoethylamine (700g) and tetrahydrofuran obtained above into a 10L three-necked flask, control the temperature of the sy...

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Abstract

The invention provides a preparation method of 2-methylethylamine, the preparation method comprises the following steps: step S1, taking 2-bromoethylamine hydrobromide as an initial raw material, and carrying out Boc protection on ethylamino in the 2-bromoethylamine hydrobromide to obtain N-Boc bromoethylamine; S2, enabling bromine in the N-Boc bromoethylamine to have a nucleophilic substitution reaction, and obtaining N-Boc-2-methoxyethylamine; S3, removing a Boc protecting group from the N-Boc-2-methoxyethylamine so as to obtain a 2-methoxyethylamine salt; and S4, carrying out a free reaction on the 2-methoxyethylamine salt under an alkaline condition so as to obtain the 2-methoxyethylamine. According to the preparation method provided by the embodiment of the invention, the intermediate steps are conventional reactions, and the operation is simple and convenient. The use of a high-toxicity methylation reagent is avoided, the generation of N-methylation is completely avoided, the quality control of raw material medicines is facilitated, and the method is environment-friendly, mild in reaction condition, simple and convenient to operate and suitable for industrial production and has good in application prospect.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-methylethylamine. Background technique [0002] 2-Methoxyethylamine is an important synthetic intermediate with good nucleophilic properties and relatively active chemical properties. It is widely used in chemical pharmaceuticals, polymer materials, flame retardants, contrast agents, metal ligands and Fine chemicals and other industries. There are reports in the literature that 2-methoxyethylamine is used as a ligand to synthesize platinum (II) complexes for the synthesis of anti-tumor, cancer and other drugs. There are also reports in the literature for the synthesis of potassium ion regulators and polymerase inhibitors as potential small molecules for the treatment of cancer. [0003] At present, the preparation method of the 2-methoxyethylamine of bibliographical information mainly contains following several kinds: [0004] 1) James first...

Claims

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Application Information

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IPC IPC(8): C07C213/06C07C217/08
CPCC07C269/04C07C269/06C07C213/06C07C271/14C07C271/16C07C217/08Y02P20/55
Inventor 蒋兆芹刘庆张海燕
Owner SUZHOU HIGHFINE BIOTECH
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