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Method for alkylating amine and amino acid

An amino acid and alkylation technology, applied in the field of amines and amino acids, can solve the problems of insufficient mechanical stability, complex reaction system, limited validity period of catalysts, etc., and achieve the effect of good industrial application prospects.

Inactive Publication Date: 2010-10-06
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This invention relates to an improved process for producing aliphatic or α -branched alkanolamines that are useful chemicals with various applications such as solvent bases used during manufacturing processes. By directly decompositing them into their corresponding alcohol without utilizing harmful substances like chloroform gas (CFC), water wastage could potentially reduce environmental concerns associated with production methods involving these compounds. Additionally, it provides ways to reuse certain types of reactants while also improving efficiency over traditional batch techniques. Overall, this new approach offers better benefits than previous methods but at lower costs compared to current methods.

Problems solved by technology

This patents describes various ways to efficiently create specific molecules called nitroiminals, including certain aliphatically charged α-,β-unsaturated carboxilanes and imido ester bases. These techniques involve complex processes involving multiple steps, leading to low yields and poor quality final products due to impurities like unreactants.

Method used

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  • Method for alkylating amine and amino acid
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  • Method for alkylating amine and amino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Synthesis of 1-benzoyl-4-methylpiperazine (8a)

[0051]

[0052]Add 1-benzoylpiperazine 7 (0.1mmol, 19mg), methanol (5mL), 10% Pd / C (100mg) to the reaction flask, pump out the air in the flask under reduced pressure, inject hydrogen, and thin layer Chromatographic monitoring, 21h after the completion of the reaction. The catalyst was removed by vacuum filtration with a water pump, and then the filter cake was washed with 5 mL of methanol, and finally the filtrate was concentrated under reduced pressure to obtain 8a (17.3 mg, 85%) as a yellow oily liquid. In the same way, 10% Pd / C (100mg) was replaced by 20% Pd (OH) 2 / C (80mg), reacted for 47h to give 8a (12.6mg, 62%). IR(film)v max : 2936, 2850, 2786, 1632, 1424, 1296, 1271, 1168, 1141, 1128, 1019, 1004cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ: 2.31(s, 3H), 2.35(br s, 2H), 2.48(br s, 2H), 3.44(br s, 2H), 3.79(br s, 2H), 7.28-7.42(s, 5H) ; 13 C NMR (100MHz, CDCl 3 )δ: 42.0, 46.0, 47.5, 55.0 (2C), 127.0, 1...

Embodiment 2

[0053] Example 2 Synthesis of 1-benzoyl-4-ethylpiperazine (8b)

[0054]

[0055] Add 1-benzoylpiperazine 7 (0.1mmol, 19mg), ethanol (5mL), 10% Pd / C (100mg) to the reaction flask, pump out the air in the flask under reduced pressure, inject hydrogen, and thin layer Chromatographic monitoring, 20h after the completion of the reaction. The catalyst was removed by filtration with a water pump under reduced pressure, then the filter cake was washed with 5 mL of ethanol, and finally the filtrate was concentrated under reduced pressure to obtain 8b (19.4 mg, 89%) as a yellow oily liquid. In the same way, 10% Pd / C (100mg) was replaced by 20% Pd (OH) 2 / C (80 mg), reacted for 44 h to give 8b (16.1 mg, 74%). IR(film)v max : 2970, 2924, 2805, 1632, 1577, 1427, 1290, 1260, 1165, 1119, 1013, cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ: 1.08(t, J=7.2Hz, 3H), 2.38(br s, 2H), 2.43(q, J=7.2Hz, 2H), 2.50(br s, 2H), 3.43(br s, 2H) , 3.79(br s, 2H), 7.36-7.40(s, 5H); 13 C NMR (100MHz, CDCl 3 )...

Embodiment 3

[0056] Example 3 Synthesis of 1-benzoyl-4-propylpiperazine (8c)

[0057]

[0058] Add 1-benzoylpiperazine 7 (0.1 mmol, 19 mg), n-propanol (5 mL), 10% Pd / C (100 mg) into the reaction flask, remove the air in the flask under reduced pressure, and inject hydrogen into the reaction flask. TLC monitoring, 30h after the completion of the reaction. The catalyst was removed by vacuum filtration with a water pump, then the filter cake was washed with 5 mL of n-propanol, and finally the filtrate was concentrated under reduced pressure to obtain 8c (17.6 mg, 76%) as a yellow oily liquid. In the same way, 10% Pd / C (100mg) was replaced by 20% Pd (OH) 2 / C (80 mg), reacted for 50 h to give 8c (21.3 mg, 92%). IR(film)v max 2964, 2921, 2866, 2805, 2765, 1632, 1427, 1372, 1293, 1278, 1159, 1015, 1001cm -1 ; 1 H NMR (500MHz, CDCl 3 )δ: 0.91(t, J=7.4Hz, 3H), 1.51(tqapparent sextet, J=7.7, 7.4Hz, 2H), 2.33(t, J=7.7Hz, 2H), 2.38(br s, 2H), 2.52(br s, 2H), 3.44(br s, 2H), 3.50(br s, 2H,)...

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Abstract

The invention relates to a method for alkylating amine and amino acid, and provides a method for alkylating amine and amino acid, which has high efficiency and chemical selectivity, and is mild and environment-friendly. The method comprises the following steps of: adding amine or amino acid, a catalyst and an alkylating reagent in a reaction flask, pumping air in the system, and introducing hydrogen to enable the whole system to be in a hydrogen atmosphere; after reaction, filtering to remove the catalyst, washing the filter cake, and decompressing and condensing the filtrate to obtain the product, wherein the catalyst is Pd/C or Pd(OH)2/C, and the alkylating reagent is alcohol. The alcohol is directly used as a substrate, and can be conveniently and easily obtained compared with halogenated hydrocarbon. In the reaction, dehydration and condensation are directly carried out to alkylate the amine, thereby halogeno salt generated by using the halogenated hydrocarbon is avoided, in addition, water is the unique side product, thereby the method is environment friendly. Documents report that in the traditional methods, the reaction condition is rigorous, and most methods are carried out under high temperature, but the method provided by the invention has mild reaction condition, and the reaction can be directly carried out under room temperature. The catalyst can be recycled, thereby the invention has very good industrial application prospect.

Description

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Claims

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Application Information

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Owner XIAMEN UNIV
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