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262368-30-9

262368-30-9

Identification

  • Product Name:N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide

  • CAS Number: 262368-30-9

  • EINECS:919-251-0

  • Molecular Weight:262.355

  • Molecular Formula: C14H22N4O

  • HS Code:2933599090

  • Mol File:262368-30-9.mol

Synonyms:N-(4-Aminophenyl)-N,4-dimethyl-1-piperazineacetamide; N-(4-Amino-phenyl)-N-methyl-2-(4-methyl-piperazin-1-yl)-acetamide; N-(4-Aminophenyl)-N,4-dimethyl-1-piperazine acetamide

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide
  • Packaging:250 mg
  • Price:$ 136
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide
  • Packaging:1 g
  • Price:$ 312
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 97%
  • Packaging:5g
  • Price:$ 1342
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 97%
  • Packaging:10g
  • Price:$ 2160
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  • Manufacture/Brand:Crysdot
  • Product Description:N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 95+%
  • Packaging:100g
  • Price:$ 317
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  • Manufacture/Brand:Chemenu
  • Product Description:N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 95%+
  • Packaging:1000g
  • Price:$ 1280
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:N-(4-AMINOPHENYL)-N-METHYL-2-(4-METHYLPIPERAZIN-1-YL)ACETAMIDE 95.00%
  • Packaging:1G
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:N-(4-AMINOPHENYL)-N-METHYL-2-(4-METHYLPIPERAZIN-1-YL)ACETAMIDE 95.00%
  • Packaging:5MG
  • Price:$ 633.99
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:N-(4-AMINOPHENYL)-N-METHYL-2-(4-METHYLPIPERAZIN-1-YL)ACETAMIDE 95.00%
  • Packaging:10MG
  • Price:$ 631.85
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:N-(4-AMINOPHENYL)-N-METHYL-2-(4-METHYLPIPERAZIN-1-YL)ACETAMIDE 95.00%
  • Packaging:1MG
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Relevant articles and documentsAll total 19 Articles be found

Synthesis of the Kinase Inhibitors Nintedanib, Hesperadin, and Their Analogues Using the Eschenmoser Coupling Reaction

Hanusek, Ji?í,Marek, Luká?,Svoboda, Jan,Váňa, Ji?í

, p. 10621 - 10629 (2021/07/31)

A novel synthetic approach involving an Eschenmoser coupling reaction of substituted 3-bromooxindoles (H, 6-Cl, 6-COOMe, 5-NO2) with two substituted thiobenzanilides in dimethylformamide or acetonitrile was used for the synthesis of eight kinase inhibitor

Preparation method of nintedanib key intermediate

-

Paragraph 0005; 0026-0039; 0045, (2021/09/08)

The invention provides a preparation method of a nintedanib key intermediate, and belongs to the technical field of synthesis of medical intermediates. The first preparation method comprises the following steps: carrying out a nitro reduction reaction on a compound IV by taking an alcohol reagent or tetrahydrofuran as a solvent, taking hydrazine hydrate as a reducing agent and taking palladium carbon (Pd/C) as a catalyst until the nitro reduction reaction is complete, performing filtering to remove the catalyst under the protection of nitrogen, performing desolventizing to remove the solvent, performing dissolving by using dichloromethane, performing filtering to remove impurities, and performing desolventizing to obtain a compound I; the second method comprises the following steps: carrying out a nitro reduction reaction on a compound IV by taking hydrazine hydrate as a reducing agent and anhydrous ferric trichloride and activated carbon as catalysts until the nitro reduction reaction is complete, performing performing filtering to remove the catalyst, performing desolventizing to remove the solvent, dissolving dichloromethane, drying anhydrous sodium sulfate, performing filtering, and performing desolventizing to obtain a compound I. The preparation method provided by the invention is high in yield, strong in operability and high in safety, belongs to an environment-friendly process, and is suitable for industrial large-scale production.

Refining method of amino intermediate

-

Paragraph 0037-0058, (2021/03/03)

The invention relates to a tefining method of an amino intermediate represented by formula (I). Through the refining method, the concentrations of a genotoxic impurity 1 (N-(4-nitrophenyl)-N-methyl-2-(4-methylpiperazin-1-yl) acetamide) and an impurity 2 (N-(4-(hydroxyamino) phenyl)-N-methyl-2- (4-methylpiperazin-1-yl) acetamide) can be controlled to 4 ppm or less. According to the present invention, the contents of the genotoxic impurity 1 and the genotoxic impurity 2 in the formula (I) are significantly reduced, such that the process guarantee is provided for the industrial preparation of high-quality nintedanib ethanesulfonate, and the medication safety is ensured.

INDOLINONE COMPOUNDS FOR USE AS MAP4K1 INHIBITORS

-

, (2020/05/15)

The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring C, X1, X2, L1, R1, R2, R3, R4, R5, R6, R7, m and n are as defined herein, which are useful as MAP4K1 inhibitors, processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by MAP4K1.

Preparation method of amino intermediate (by machine translation)

-

Paragraph 0036; 0038, (2020/02/20)

Compared with an existing preparation method, the method for preparing. the amine-based (I) intermediate disclosed by the invention comprises the following, steps: carrying (III) out condensation, reduction and the like of the compound of. the formula I to obtain, the target compound (I), and 1 remarkably reducing the, content of the impurities in the obtained compound according to the, invention as compared with the existing preparation. method. (by machine translation)

Process route upstream and downstream products

Process route

2-chloro-N-methyl-N-(4-nitrophenyl)acetamide
2653-16-9

2-chloro-N-methyl-N-(4-nitrophenyl)acetamide

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: toluene / 30 - 50 °C
2: palladium on activated charcoal; hydrogen
With palladium on activated charcoal; hydrogen; In toluene;
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 12 h / 20 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 2585.81 Torr
With palladium 10% on activated carbon; hydrogen; potassium carbonate; In methanol; acetone;
Multi-step reaction with 2 steps
1: toluene / 2 h / 55 °C
2: palladium on activated charcoal; hydrogen / isopropyl alcohol / 12 h / 20 °C
With palladium on activated charcoal; hydrogen; In isopropyl alcohol; toluene;
Multi-step reaction with 2 steps
1: toluene / 2 h / 55 °C
2: palladium on activated charcoal; hydrogen / isopropyl alcohol / 12 h / 20 °C
With palladium on activated charcoal; hydrogen; In isopropyl alcohol; toluene;
Multi-step reaction with 2 steps
1: 5 h / 20 - 25 °C
2: palladium on activated charcoal; hydrogen / 18 h / 40 - 55 °C / 2068.65 - 2327.23 Torr
With palladium on activated charcoal; hydrogen;
Multi-step reaction with 2 steps
1: toluene / 2 h / 20 - 60 °C / Large scale
2: palladium 10% on activated carbon; hydrogen / toluene; isopropyl alcohol / 20 - 30 °C / 750.08 - 1500.15 Torr / Large scale
With palladium 10% on activated carbon; hydrogen; In isopropyl alcohol; toluene;
Multi-step reaction with 2 steps
1: ethyl acetate / 2 h / 40 - 50 °C
2: palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 20 °C
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; isopropyl alcohol;
1-methyl-piperazine
109-01-3

1-methyl-piperazine

2-chloro-N-methyl-N-(4-nitrophenyl)acetamide
2653-16-9

2-chloro-N-methyl-N-(4-nitrophenyl)acetamide

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
1-methyl-piperazine; 2-chloro-N-methyl-N-(4-nitrophenyl)acetamide; In toluene; at 40 - 55 ℃; for 2.5h;
With hydrogen; palladium on activated charcoal; In isopropyl alcohol; toluene; at 20 ℃; under 750.075 Torr;
70.5%
2-chloro-N-methyl-N-(4-nitrophenyl)acetamide; In ethyl acetate; at 40 ℃; for 0.5h;
1-methyl-piperazine; In ethyl acetate; at 40 - 50 ℃; for 2h;
With palladium on activated charcoal; hydrogen; at 25 ℃; for 2h; under 18751.9 Torr;
400 mg
N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)-acetamide
1139453-98-7

N-methyl-2-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)-acetamide

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
With 5%-palladium/activated carbon; hydrazine hydrate; In ethanol; at 0 - 40 ℃; for 1h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; Large scale;
97.3%
With palladium 10% on activated carbon; hydrogen; In isopropyl alcohol; toluene; at 20 - 30 ℃; under 750.075 - 1500.15 Torr; Large scale;
88.1%
With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1.5h; under 2585.81 Torr;
83%
With trichlorosilane; triethylamine; In chloroform; at 20 ℃;
83.6%
With hydrogen; palladium 10% on activated carbon; In isopropyl alcohol; toluene; at 20 ℃; under 3000.3 Torr; Product distribution / selectivity;
With hydrogen; palladium 10% on activated carbon; In ethyl acetate; at 20 ℃; under 3750.38 Torr; Product distribution / selectivity;
With hydrogen; palladium 10% on activated carbon; In isopropyl alcohol; toluene; at 20 ℃; under 3000.3 Torr; Product distribution / selectivity;
With hydrogen; palladium 10% on activated carbon; In ethyl acetate; isopropyl alcohol; at 20 ℃; under 3750.38 Torr; Product distribution / selectivity;
With palladium on activated charcoal; hydrogen;
With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 2h; under 2585.81 Torr;
3.4 g
With palladium 10% on activated carbon; hydrogen; In isopropyl alcohol; at 20 ℃; for 3h;
With palladium on activated charcoal; hydrogen; In isopropyl alcohol; at 20 ℃; for 12h;
With palladium on activated charcoal; hydrogen; In isopropyl alcohol; at 20 ℃; for 12h;
With palladium on activated charcoal; hydrogen; at 40 - 55 ℃; for 18h; under 2068.65 - 2327.23 Torr; Pressure;
With palladium 10% on activated carbon; hydrogen; In isopropyl alcohol; at 20 ℃;
1-methyl-piperazine
109-01-3

1-methyl-piperazine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
chloroacetyl chloride; N-methyl(p-nitroaniline); In ethyl acetate; at 50 - 55 ℃; for 2h;
1-methyl-piperazine; at 45 - 50 ℃; for 4.5h; Solvent;
79.27%
tert-butyl 4-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)phenylcarbamate

tert-butyl 4-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)phenylcarbamate

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
With trifluoroacetic acid; at 60 ℃; for 2h; Inert atmosphere;
79%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

4-Fluoronitrobenzene
350-46-9,178603-76-4

4-Fluoronitrobenzene

methylamine
74-89-5

methylamine

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
4-Fluoronitrobenzene; methylamine; In dimethyl sulfoxide;
chloroacetyl chloride; In toluene;
1-methyl-piperazine; Further stages;
58%
para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 16 h / 20 °C / Heating; Sealed tube
2: lithium carbonate / 1,4-dioxane; water / 3 h / 33 °C
3: potassium carbonate / acetone / 12 h / 20 °C
4: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 2585.81 Torr
With palladium 10% on activated carbon; hydrogen; lithium carbonate; potassium carbonate; In 1,4-dioxane; methanol; water; acetone;
Multi-step reaction with 3 steps
1.1: water / 16 h / 90 °C / Sealed tube
2.1: ethyl acetate / 1 h / 70 °C
2.2: 2 h / Reflux
3.1: ethyl acetate / 0.5 h / 40 °C
3.2: 2 h / 40 - 50 °C
3.3: 2 h / 25 °C / 18751.9 Torr
In water; ethyl acetate;
1-methyl-piperazine
109-01-3

1-methyl-piperazine

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: toluene / 2 h / 20 - 60 °C / Large scale
2: palladium 10% on activated carbon; hydrogen / toluene; isopropyl alcohol / 20 - 30 °C / 750.08 - 1500.15 Torr / Large scale
With palladium 10% on activated carbon; hydrogen; In isopropyl alcohol; toluene;
Multi-step reaction with 2 steps
1: ethyl acetate / 2 h / 40 - 50 °C
2: palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 20 °C
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; isopropyl alcohol;
N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

Conditions
Conditions Yield
N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine
262368-30-9

N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine

(E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester
1168152-07-5

(E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester

Conditions
Conditions Yield
N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine; (E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; With methanol; In N,N-dimethyl-formamide; at 75 ℃; for 4h; Large scale;
With methanol; potassium hydroxide; In N,N-dimethyl-formamide; Temperature; Large scale;
94.6%
N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine; (E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; In methanol; for 5h; Reflux;
With potassium hydroxide; In methanol; at 20 - 70 ℃; for 0.5h; Concentration; Reagent/catalyst; Temperature; Solvent;
90%
N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine; (E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; In methanol; N,N-dimethyl-formamide; Reflux;
With piperidine; In methanol; N,N-dimethyl-formamide; Reflux;
88%
N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine; (E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; In methanol; for 5h; Reflux;
With potassium hydroxide; In methanol;
84%
N-[(4-methyl-piperazin-1-yl)methylcarbonyl]-N-methyl-p-phenylendiamine; (E)-1-acetyl-3-(methoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; In N,N-dimethyl-formamide; at 80 ℃; for 1h;
With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
77%

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