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Method for preparing 2-amino-dimethyl acetamide hydrochloride

A technology of dimethylacetamide and hydrochloride, which is applied in the preparation of carboxylic acid amides, chemical instruments and methods, and the preparation of organic compounds, and can solve the problems of unsuitability for large-scale production, complicated operation procedures, and high cost of condensing agent raw materials. problems, to achieve the effect of cheap raw materials, stable process and mild reaction conditions

Active Publication Date: 2014-03-19
ASYMCHEM LAB FUXIN
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  • Abstract
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Problems solved by technology

The synthesis method of 2-amino-N,N-dimethylacetamide hydrochloride reported at this stage mainly uses Boc-glycine as the starting material, and obtains 2-amino-N,N through ammonolysis and deprotection salt formation. -Dimethylacetamide hydrochloride (Tetrahedron Letters, 1997, vol.38, #17 P.3039-3042), wherein the ammonolysis step must use the condensation agent HOBt and EDC / HCl (US2008 / 318923) or CDI ( Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972~1999); nb.3; (1991); p.387~392) to activate the carboxylic acid, the condensing agent must be removed after the reaction, and the operation process is complicated , and the raw material cost of the condensing agent used is relatively high, which is not suitable for large-scale production

Method used

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  • Method for preparing 2-amino-dimethyl acetamide hydrochloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A method for preparing 2-amino-N, N-dimethylacetamide hydrochloride, characterized in that the specific preparation steps are as follows:

[0023] (1) Amino protection: Add 55L (1.0eq) of 15% aqueous sodium carbonate solution, 50L (5mL / g) of dichloromethane, and 17.4kg (1.0eq) of di-tert-butyl dicarbonate into a 200L reactor in sequence, and the main raw material Glycine methyl ester hydrochloride 10kg, stirred and reacted at 0±2°C for 2 hours. After the reaction was completed, the liquids were separated, the aqueous phase was extracted with dichloromethane, the organic phase was combined with salt, washed with salt and then concentrated to obtain 14.5 kg of Boc-glycine methyl ester with a yield of 96.2% and a GC purity of 98.8%.

[0024] The NMR data of Boc-glycine methyl ester are as follows:

[0025] 1 H NMR (300MHZ, CDCl3), δ1.38 (H of tert-butyl 3 methyl groups), δ3.68 (H on methyl ester), δ3.90 (H on methylene), δ7.90 ( H on amino)

[0026] (2) Ammonolysis: Ad...

Embodiment 2

[0033] A method for preparing 2-amino-N, N-dimethylacetamide hydrochloride, characterized in that the specific preparation steps are as follows:

[0034](1) Amino group protection: Add 1kg of main raw materials glycine methyl ester hydrochloride, 15L of methyl tert-butyl ether (15mL / g), and 3.3kg of N-methylmorpholine (4.0eq) into a 50L reaction flask in sequence, and cool down To 30±2°C, add 3.5kg (2.0eq) of di-tert-butyl dicarbonate dropwise, and keep the reaction at 30±2°C for 1-2 hours after dropping. After the reaction is completed, concentrate until there is no solvent, add 6L of water, keep stirring for 1 to 2 hours, filter to obtain Boc-glycine methyl ester, and dry to obtain 1.44kg, the yield is 95.5%, and the GC purity is 98.9%;

[0035] The NMR data of Boc-glycine methyl ester are as follows:

[0036] 1 H NMR (300MHZ, CDCl3), δ1.42 (H of tert-butyl 3 methyl groups), δ3.56 (H on methyl ester), δ3.88 (H on methylene), δ7.87 ( H on the amino group).

[0037] (2) Am...

Embodiment 3

[0044] A method for preparing 2-amino-N, N-dimethylacetamide hydrochloride, characterized in that the specific preparation steps are as follows:

[0045] (1) Amino group protection: Add 25kg of the main raw materials glycine methyl ester hydrochloride, 200L (8mL / g) of tetrahydrofuran (8mL / g), 50.4kg (2.5eq) of triethylamine to a 500L reactor in sequence, cool down to 15±2°C, add dropwise 52.2kg (1.2eq) of di-tert-butyl dicarbonate, after dropping, keep it at 15±2℃ for 1~2h. After the reaction was completed, water was added, the liquid was separated, the organic phase was concentrated, the temperature was lowered, and 36 kg of Boc-glycine methyl ester was obtained by crystallization, with a yield of 95.5% and a GC purity of 99.4%.

[0046] The NMR data of Boc-glycine methyl ester are as follows:

[0047] 1 H NMR (300MHZ, CDCl3), δ1.40 (H of tert-butyl 3 methyl groups), δ3.67 (H on methyl ester), δ3.92 (H on methylene), δ7.95 ( H on the amino group).

[0048] (2) Ammonolysis...

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Abstract

A method for preparing 2-amino-dimethyl acetamide hydrochloride. An initial raw material is selected from commercialized raw material or easily prepared glycine methyl ester hydrochloride and is prepared into 2-amino-dimethyl acetamide hydrochloride by amino protection, aminolysis and deprotection. The invention has advantages of cheap and easily available raw material, mild reaction conditions, stable technology, a stable overall yield at 78-84%, a stable object product purity higher than 99%, and intermediates obtained by direct separation with a purity higher than 98%. Meanwhile operations of the whole production process are simple and without generation of three wastes (waste gas, waste water and industrial residue) so as to save production costs substantially. The method is suitable for large scale production and provides a new thinking and approach for preparation of 2-amino-dimethyl acetamide hydrochloride.

Description

(1) Technical field: [0001] The invention relates to the field of organic synthesis and preparative chemistry, in particular to a method for preparing 2-amino-N,N-dimethylacetamide hydrochloride. (two) background technology: [0002] Glycylamide and its derivatives have been widely used in the fields of biology, medicine, and chemical industry. Ernest Koenigs et al. (Koenigs E, Mylo B, Ber. 1909, 41:4427) in Germany were the first to synthesize glycinamide compounds. Later, hundreds of such compounds were synthesized in order to find some anesthetics with local anesthetic effects similar to cocaine but not addictive, among which lidocaine, prilocaine, and mepicaine showed great Good anesthetic effect (Dong Tingwei, Gu Minmin, Wu Shiyun, etc. Modern Organic Chemistry Experiments. Shanghai Translation Press. 1987.312), thus promoting extensive research on this type of compound, such as being used as a substituted N-(indole Indole-2-carbonyl) glycinamide (CN1142492), bicyclic ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/06C07C231/12
Inventor 洪浩韦建丰惜春
Owner ASYMCHEM LAB FUXIN
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