137-58-6

Usage

InChI:InChI=1/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)/p+1

Synthetic route

diethylamine (109-89-7) + 2-chloro-N-(2,6-dimethylphenyl)acetamide (1131-01-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 99℃; under 5171.62 Torr; Temperature; Flow reactor;	98%
at 40℃; for 6h; Temperature;	97%
In hexane at 60℃; Temperature; Reflux;	91.1%

diethylamine (109-89-7) + chloroacetyl chloride (79-04-9) + 2,6-dimethylaniline (87-62-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
Stage #1: chloroacetyl chloride; 2,6-dimethylaniline In toluene at 80 - 90℃; for 3h; Large scale; Stage #2: With sodium carbonate; potassium iodide In water; toluene for 0.5h; Large scale; Stage #3: diethylamine In water; toluene Solvent; Temperature; Reagent/catalyst; Large scale;	95.2%
With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 120 - 130℃; under 12929 Torr;

(2-diethylaminoethyl)amide (7409-48-5) + 2,6-dimethylaniline (87-62-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry;	95%

denatonium benzoate (3734-33-6) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 2-diethylamino-N-(2,6-dimethyl-phenyl)-3-phenyl-propionamide

Conditions	Yield
at 250℃;

2,6-dimethylaniline (87-62-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sodium acetate 2: benzene View Scheme
Multi-step reaction with 2 steps 1: triethylamine / chloroform / 0.02 h / Flow reactor 2: triethylamine / N,N-dimethyl-formamide / 0.19 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sodium acetate / water / 24 h / Reflux 2: triethylamine / 1,4-dioxane / 120 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: dichloromethane / 105 °C / 12929 Torr / Flow reactor 2: triethylamine / N,N-dimethyl-formamide / 99 °C / 5171.62 Torr / Flow reactor View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 3 h / 20 °C 2: acetone / 8 h / Reflux View Scheme

[(2,6-dimethylphenylcarbamoyl)methyl]diethyl-(2-phosphonooxybenzyl)ammonium trifluoroacetate disodium salt → salicylic alcohol (90-01-7) + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
With alkaline phosphatase In water at 37℃; for 6h; pH=7.4; Enzyme kinetics; Enzymatic reaction;

[(2,6-dimethylphenylcarbamoyl)methyl]diethyl-(2-phosphonooxybenzyl)ammonium trifluoroacetate disodium salt → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
With rat lung homogenate at 37℃; for 3h; Enzyme kinetics;

[(2,6-dimethylphenylcarbamoyl)methyl]diethyl-(4-phosphonooxybenzyl)ammonium trifluoroacetate disodium salt → (4-hydroxyphenyl)methanol (623-05-2) + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
With alkaline phosphatase In water at 37℃; for 6h; pH=7.4; Enzyme kinetics; Enzymatic reaction;

C14H22N2O*C56H98O35 (178421-96-0) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + heptakis(2,6-di-O-methyl)cyclomaltoheptaose (51166-71-3)

Conditions	Yield
With pluronic copolymer F290 In water at 25℃; Equilibrium constant; Reagent/catalyst;

N,N-diethylglycine methyl ester (30280-35-4) + 2,6-dimethylaniline (87-62-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
With sodium methylate at 95℃; for 0.5h; Concentration; Temperature;

2.6-dimethylphenol (576-26-1) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide; 2,6-dimethylcyclohexanone; 5%-palladium/activated carbon / 5 h / 180 °C 2: sodium methylate / 0.5 h / 95 °C View Scheme

2,6-dimethylnitrobenzene (81-20-9) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 5%-palladium/activated carbon; hydrogen / methanol / 20 - 25 °C 2.1: potassium carbonate / dichloromethane 2.2: 1 h / 20 °C 3.1: hexane / 60 °C / Reflux View Scheme

2-(N-ethylacetamido)2',6'-dimethylacetanilide → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
With borane-THF In tetrahydrofuran at 20℃;	176 mg

2,6-dimethylphenyl isonitrile (119072-54-7, 2769-71-3) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 45 °C 2: borane-THF / tetrahydrofuran / 20 °C View Scheme

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + stearic acid (57-11-4) → C14H22N2O*C18H36O2 (1001438-56-7)

Conditions	Yield
for 0.0833333h; Inert atmosphere; Heating;	100%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → lidocaine hydrochloride (73-78-9)

Conditions	Yield
With hydrogenchloride In diethyl ether	100%
With hydrogenchloride; pyrographite In water; 1,2-dichloro-ethane for 0.333333h; pH=3.5; pH-value;	88.72%
With hydrogenchloride In water; acetone at 20℃; pH=<= 4;	80.6%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 4-((1,3-bis(octanoyloxy)propan-2-yl)oxy)-4-oxobutanoic acid (150994-82-4) → 2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium 4-((1,3-bis(octanoyloxy)propan-2-yl)oxy)-4-oxobutanoate

Conditions	Yield
In acetonitrile at 50℃; for 6h;	100%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → C14H17(2)H5N2O

Conditions	Yield
With [(2)H6]acetone; tris(pentafluorophenyl)borate In toluene at 150℃; for 3h; Inert atmosphere;	99%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + bromoacetic acid methyl ester (96-32-2) → 2-((2,6-dimethylphenyl)amino)-N,N-diethyl-N-(2-methoxy-2-oxoethyl)-2-oxoethan-1-aminium bromide

Conditions	Yield
In acetonitrile at 80℃; for 1h; Inert atmosphere;	97%
In acetonitrile at 60℃;

gluconic acid (526-95-4) + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → 2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate

Conditions	Yield
In ethanol for 5h; pH=2 - 7;	95%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → N-(4-chloro-2,6-dimethylphenyl)-2-(diethylamino)-acetamide

Conditions	Yield
With trichloroisocyanuric acid; brilliant green carbocation In acetonitrile at 20℃; for 0.166667h; Irradiation; regioselective reaction;	94%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → lidocaine N-oxide (2903-45-9)

Conditions	Yield
With perfluoro-cis-2-n-butyl-3-n-propyloxaziridine; HCFC-225ca,cb In dichloromethane at -60℃; for 0.333333h;	93%
With dihydrogen peroxide In methanol at 20℃; for 42h;	71%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane
With rat liver microsomes; NADPH In water Product distribution;

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + (4-bromomethylbenzyl)carbamic acid tert-butyl ester (187283-17-6) → C27H40N3O3(1+)*Br(1-)

Conditions	Yield
at 80℃; for 0.166667h;	91%
at 80℃; for 0.166667h;	91%

acetoxymethyl bromide (590-97-6) + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → N-(acetoxymethyl)-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium bromide

Conditions	Yield
In acetonitrile at 80℃; for 1h; Inert atmosphere;	90%
In 1,2-dichloro-ethane at 100℃; for 6h; Sealed tube;	40%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 4-tetradecylbenzenesulfonic acid (47377-16-2) → lidocaine 4-tetradecylbenzenesulfonate

Conditions	Yield
In isopropyl alcohol Heating;	90%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + tetramethylammonium fluoride (373-68-2) → 2-(diethylamino)-N-(2,6-dimethylphenyl)-N-methylacetamide (31058-85-2)

Conditions	Yield
In toluene at 100℃; for 12h;	88%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 4-octadecylbenzenesulfonic acid (79840-57-6) → lidocaine 4-octadecylbenzenesulfonate

Conditions	Yield
In ethanol; water Heating;	87%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → 2-diethylamino-N-(2,6-dimethyl-3-nitro-phenyl)-acetamide (39942-49-9)

Conditions	Yield
With sulfuric acid; nitric acid In water at 0 - 25℃; for 0.75h;	86%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + C31H60O8S*C5H5N → C31H60O8S*C14H22N2O

Conditions	Yield
In methanol at 20℃; for 0.5h;	85%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → C14H15(2)H7N2O

Conditions	Yield
With d8-isopropanol; 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In toluene at 170℃; for 2h; Inert atmosphere; Microwave irradiation; Sealed tube;	84%
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); d8-isopropanol In toluene at 170℃; under 12751.3 Torr; for 2h; Microwave irradiation; Inert atmosphere; Sealed tube;	84%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → C14H20(2)H2N2O

Conditions	Yield
With tetrakis(tetrabutylammonium)decatungstate(VI); 2,4,6-Triisopropylthiophenol; water-d2; trifluoroacetic acid In acetonitrile Irradiation;	84%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + (2,6-dichlorophenyl)cyanamide (21714-23-8) + palladium diacetate (3375-31-3) → K[Pd(2,6-Cl2pcyd)2(LC)]

Conditions	Yield
Stage #1: (2,6-dichlorophenyl)cyanamide With potassium hydroxide In ethanol Reflux; Stage #2: 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide; palladium diacetate With triethylamine In ethanol at 20℃; for 48h; pH=7;	83.33%

ammonium hexafluorophosphate + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → C24H36ClN2ORu(1+)*F6P(1-)

Conditions	Yield
Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide In acetone at 20℃; for 5h; Inert atmosphere; Schlenk technique; Stage #2: ammonium hexafluorophosphate Inert atmosphere; Schlenk technique;	81.2%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 2-bromoethanol (540-51-2) → 2-(2,6-dimethylphenylamino)-N,N-diethyl-N-(2-hydroxyethyl)-2-oxoethanaminium bromide

Conditions	Yield
at 100℃; for 8h;	81.2%
at 90℃; for 24h; Temperature; Sealed tube;	31%
at 90℃; for 24h;	27.6%
at 80℃;

2,6-dimethylphenylcyanamide (20922-60-5) + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + palladium diacetate (3375-31-3) → K[Pd(2,6-Me2pcyd)2(LC)]

Conditions	Yield
Stage #1: 2,6-dimethylphenylcyanamide With potassium hydroxide In ethanol Reflux; Stage #2: 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide; palladium diacetate With triethylamine In ethanol at 20℃; for 48h; pH=7;	81.14%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 1-bromo-3-propanol (627-18-9) → N-(2-(2,6-dimethylphenylamino)-2-oxoethyl)-N,N-diethyl-3-hydroxypropan-1-aminium bromide

Conditions	Yield
at 110℃; for 8h;	80.3%
at 80℃;

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 2,6-diethylphenylcyanamide + palladium diacetate (3375-31-3) → K[Pd(2,6-Et2pcyd)2(LC)]

Conditions	Yield
Stage #1: 2,6-diethylphenylcyanamide With potassium hydroxide In ethanol Reflux; Stage #2: 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide; palladium diacetate With triethylamine In ethanol at 20℃; for 48h; pH=7;	79.25%

potassium cyanide + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → 2-((1-cyanoethyl)(ethyl)amino)-N-(2,6-dimethyl-phenyl)acetamide

Conditions	Yield
With 2-Picolinic acid; iron(III) chloride; tert-Butyl peroxybenzoate; 18-crown-6 ether In acetonitrile at 50℃; for 48h;	77%

dichlorobis(dimethyl sulfoxide)platinum(II) + 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + 3,5-dichlorophenylcyanamide + potassium hydroxide → K[Pt(3,5-(Cl2)2pcyd)2(LC)]

Conditions	Yield
Stage #1: 3,5-dichlorophenylcyanamide; potassium hydroxide In ethanol Reflux; Stage #2: dichlorobis(dimethyl sulfoxide)platinum(II); 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide With triethylamine In ethanol at 20℃; pH=Ca. 7;	76.55%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → N-(3-chloro-2,6-dimethylphenyl)-2-(diethylamino)acetamide

Conditions	Yield
With hydrogen fluoride; antimony pentafluoride; sodium chloride at -20℃;	75%
With hydrogenchloride; [bis(acetoxy)iodo]benzene In water; 1,2-dichloro-ethane at 50℃; for 2h; Reagent/catalyst; regioselective reaction;	60%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) + acetic anhydride (108-24-7) → 2-(N-ethylacetamido)2',6'-dimethylacetanilide

Conditions	Yield
With 1H-imidazole; iodosylbenzene; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III) In dichloromethane; acetonitrile at 20℃; for 3h;	74%

Upstream product

• 109-89-7 diethylamine 
• 1131-01-7 2-chloro-N-(2,6-dimethylphenyl)acetamide 
• 3734-33-6 denatonium benzoate 
• 178421-96-0 C₁₄H₂₂N₂O*C₅₆H₉₈O₃₅ 
• 7409-48-5 (2-diethylaminoethyl)amide 
• 87-62-7 2,6-dimethylaniline 
• 81-20-9 2,6-dimethylnitrobenzene 
• 79-04-9 chloroacetyl chloride 
• 2644-21-5 ethyl N,N-diethylglycinate 
• 119072-54-7 2,6-dimethylphenyl isonitrile 
• 576-26-1 2.6-dimethylphenol 
• 30280-35-4 N,N-diethylglycine methyl ester 

Downstream Products

• 24003-58-5 Lidocaine N-ethyl bromide 
• 5369-03-9 QX-314 
• 109366-65-6 1-(α-Diaethylamino-thioacetylamino)-2,6-dimethyl-benzol 
• 2903-45-9 lidocaine N-oxide 
• 75889-35-9 2-Diethylamino-N-(2,6-dimethyl-phenyl)-N-(2-ethoxy-ethyl)-acetamide 
• 75889-33-7 2-Diethylamino-N-(2,6-dimethyl-phenyl)-N-(2-hydroxy-ethyl)-acetamide 
• 1674-99-3 denatonium chloride 
• 1234389-43-5 lidocaine ibuprofenate-salicylic acid 
• 1234188-59-0 ephedrinium-lidocaine salicylate 
• 1234188-61-4 ephedrinium-lidocaine ibuprofenate 
• 178421-96-0 C₁₄H₂₂N₂O*C₅₆H₉₈O₃₅ 
• 39942-41-1 4-hydroxylidocaine 
• 34604-55-2 3-Hydroxylidocaine 
• 7728-40-7 N-(2,6-dimethylphenyl)-2-ethylaminoacetamide 

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Preparation method of lidocaine hydrochloride

The invention relates to a preparation method of lidocaine hydrochloride, which comprises the following steps: carrying out acylation reaction by using 2, 6-dimethylaniline and chloroacetyl chloride as raw materials, directly adding diethylamine into the system to carry out amination reaction after the reaction is finished, filtering the product, and adding hydrochloric acid into the filtrate to carry out salification reaction. The preparation method of lidocaine hydrochloride provided by the invention is a one-pot method, avoids repeated purification of an intermediate product in a traditional process, and is simple in process, mild in condition, easy to control, high in product yield and high in purity.

Method for preparing lidocaine intermediate alpha-chloroacetyl-2, 6-dimethylaniline and lidocaine without adding extra alkali

The invention relates to a method for preparing lidocaine intermediate alpha-chloroacetyl-2, 6-dimethylaniline and lidocaine without adding extra alkali, which belong to the technical field of organicsynthesis. The invention discloses the method for preparing alpha-chloroacetyl-2, 6-dimethylaniline, which comprises the following steps: in the process of generating alpha-chloroacetyl-2, 6-dimethylaniline by carrying out a chloroacetylation reaction on 2, 6-dimethylaniline and chloroacetyl chloride, taking one or a mixed solution of more than two of an alkane solvent, an ether solvent and an ester solvent as an organic solvent. No extra alkali is added, so that the separation process can be reduced; the method can be applied to one-pot reaction to directly prepare lidocaine, namely, 2, 6-dimethylaniline, chloroacetyl chloride and diethylamine directly react to obtain lidocaine, the method is simple, no extra alkali is added, the separation process is simplified, the used solvents are three types of solvents, operation is safer, and the obtained product is high in purity, high in yield, low in cost and environmentally friendly.

Method for preparing lidocaine

The invention discloses a method for preparing lidocaine. The method comprises the following steps of: (1) by using 2, 6-dimethylnitrobenzene as a raw material, Pd/C as a catalyst and methanol as a solvent, carrying out reduction reaction with hydrogen at normal temperature and normal pressure to obtain an intermediate 2, 6-dimethylaniline; (2) reacting the obtained intermediate 2, 6-dimethylaniline with chloroacetyl chloride in the presence of potassium carbonate, and taking dichloromethane as a solvent to prepare an intermediate chloroacetyl-2, 6-dimethylaniline; and (3) reacting the obtained intermediate chloroacetyl-2, 6-dimethylaniline with diethylamine, taking normal hexane as a solvent, performing refluxing until the reaction is complete, performing washing with water and cooling toobtain lidocaine. The method disclosed by the invention is simple and convenient in technological process, few in operation links and relatively high in lidocaine yield, and the prepared lidocaine isgood in purity which reaches 99.5% or above, so that the method has a good industrial application prospect.

Method for preparing lidocaine by continuous reaction (by machine translation)

The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for preparing lidocaine by continuous reaction. To the method, the continuous reaction is adopted, and the crystallization of intermediate chloroacetyl -2 and 6 -dimethylaniline is not needed. The lidocaine finished product can be directly obtained through separation, purification and other treatment and drying processes, and the molar yield 93% or above can be obtained. The process operation is simplified, the solvent recovery sleeve is used, the sewage discharge amount is reduced, the production cost is reduced, energy conservation and consumption reduction are realized, and the technology is green and environment-friendly. (by machine translation)

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