Method for synthesizing [<2>H3]-1-methylamino-2-phenylpropane

A technology of phenylpropane and synthetic method, which is applied in the field of forensic drug analysis, can solve the problems of harsh reaction conditions, time-consuming, time-consuming and cumbersome operations, etc., and achieve the effects of short reaction time, simple operation and short synthetic route

Active Publication Date: 2018-11-23
INST OF FORENSIC SCI OF MIN OF PUBLIC SECURITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This strategy has the problems of harsh reaction conditions and time-consuming and cumbersome operations, and alkyl chloroformate is a highly toxic chemical, which requires high skills for experimental operators; at the same time, the synthetic routes of these two methods have long steps and time-consuming Many, do not meet the requirements of green chemistry

Method used

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  • Method for synthesizing [&lt;2&gt;H3]-1-methylamino-2-phenylpropane
  • Method for synthesizing [&lt;2&gt;H3]-1-methylamino-2-phenylpropane
  • Method for synthesizing [&lt;2&gt;H3]-1-methylamino-2-phenylpropane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034](1) 201 milligrams of phenylacetone and 150 milligrams of deuterated methylamine hydrochloride were added to 5 milliliters of methanol successively, and nitrogen protection was replaced. Under cooling in an ice bath, add 0.13 ml of tetraisopropyl titanate and 0.07 ml of triethylamine sequentially with a needle [need to activate phenylacetone with tetraalkyl titanate first, then add triethylamine to release deuteroformazine Amine, and finally deuterated methylamine and activated phenylacetone undergo addition reaction], start stirring. Monitor the reaction with GC / MS to generate the first intermediate (m / z43, 59, 91, 147), and stop the reaction after the phenylacetone (m / z 43, 92, 134) is completely consumed, and the reaction time is 5- 20 hours without post-treatment.

[0035] (2) Continue cooling with an ice bath, and add 90 mg of sodium borohydride in three batches under stirring. The reaction was monitored by GC / MS to produce [ 2 h 3 ]-1-methylamino-2-phenylpropan...

Embodiment 2

[0038] (1) 201 milligrams of phenylacetone and 150 milligrams of deuterated methylamine hydrochloride were added to 10 milliliters of ethanol successively, and nitrogen protection was replaced. Under cooling in an ice bath, add 0.15 ml of tetraethyl titanate and 0.10 ml of triethylamine sequentially with a needle [it is necessary to activate phenylacetone with tetraalkyl titanate first, and then add triethylamine to release deuterated methylamine. Finally, deuterated methylamine and the activated phenylacetone undergo an addition reaction] and start stirring. The reaction was monitored by GC / MS, and the first intermediate (m / z 43, 59, 91, 147) was generated. After the phenylacetone (m / z 43, 92, 134) was completely consumed, the reaction was stopped without post-treatment .

[0039] (2) Continue cooling with an ice bath, and add 100 mg of sodium borohydride in three batches under stirring. The reaction was monitored by GC / MS to produce [ 2 h 3 ]-1-methylamino-2-phenylpropan...

Embodiment 3

[0042] (1) 201 milligrams of phenylacetone, 225 milligrams of anhydrous sodium carbonate and 1.1 milliliters of 2mol / L deuterated methylamine methanol solution were added to 4 milliliters of methanol successively to replace the nitrogen protection. Under cooling in an ice bath, 0.15 ml of tetraisopropyl titanate was added with a needle, and stirring was started. The reaction was monitored by GC / MS, and the first intermediate (m / z 43, 59, 91, 147) was generated. After the phenylacetone (m / z 43, 92, 134) was completely consumed, the reaction was stopped without post-treatment.

[0043] (2) Continue cooling with an ice bath, and add 100 mg of potassium borohydride in three batches under stirring. The reaction was monitored by GC / MS to produce [ 2 h 3 ]-1-methylamino-2-phenylpropane (m / z 43,61,91), after the first reaction intermediate (m / z 43,59,91,147) is completely consumed, stop the reaction.

[0044] (3) Carefully add 4 ml of 2 mol / L ammonia solution to quench the reaction...

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Abstract

The invention discloses a method for synthesizing [<2>H3]-1-methylamino-2-phenylpropane. The method is characterized by comprising the following steps: (1) subjecting phenylacetone, deuterated methylamine and tetraalkyl titanate or phenylacetone, deuterated methylamine, tetraalkyl titanate and an acid binding agent or phenylacetone, deuterated methylamine hydrochloride and tetraalkyl titanate to areaction, so as to obtain a first intermediate; (2) subjecting the first intermediate obtained in the step (1) and a reduction reagent to a reaction; (3) adding ammonia water into the step (2) for aquenching reaction, carrying out suction filtration to remove precipitates, carrying out precipitation with an organic solvent, merging liquid, and carrying out extraction and knockout to collect an organic phase, thereby obtaining the [<2>H3]-1-methylamino-2-phenylpropane. The method has the advantages that the synthesis route is short, the operation is simple and safe, the reaction time is short, and the yield exceeds 50%. Through further purification, both the purity and deuterated rate of the [<2>H3]-1-methylamino-2-phenylpropane can reach 99.5% or more, and thus, the [<2>H3]-1-methylamino-2-phenylpropane completely can serve as a deuterated internal reference substance for a mass-spectrum internal reference quantitative analysis method.

Description

technical field [0001] The invention relates to the field of forensic drug analysis. More specifically, involves [ 2 h 3 The synthetic method of ]-1-methylamino-2-phenylpropane. Background technique [0002] At present, the most effective qualitative and quantitative analysis method internationally recognized is mass spectrometry (MS) internal standard analysis. When mass spectrometry (MS) internal standard method is used for analysis, in order to obtain the most reliable and accurate analysis results, the best internal standard is the deuterated substance of each sample. To establish an internal standard analysis method for accurate qualitative and quantitative analysis of methamphetamine, the best internal standard substance-deuterated 1-methylamino-2-phenylpropane is urgently needed. [0003] However, at present, there is no mass production and sales of deuterated 1-methylamino-2-phenylpropane in China, and deuterated 1-methylamino-2-phenylpropane is completely depe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/28C07C209/68C07C211/27C07B59/00
CPCC07B59/001C07B2200/05C07C209/68C07C211/27
Inventor 赵彦彪高利生郑珲张春水郑晓雨钱振华常颖赵阳翟晚枫李彭杨虹贤刘克林
Owner INST OF FORENSIC SCI OF MIN OF PUBLIC SECURITY
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