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    Home > 4-(4-Methyl-1-piperazinylmethyl)benzoic acid
    4-(4-Methyl-1-piperazinylmethyl)benzoic acid structure

    4-(4-Methyl-1-piperazinylmethyl)benzoic acid

    • CAS No:

      106261-48-7

    • Formula:

      C13H18N2O2

    • Synonyms:

      4-(4-Methylpiperazin-1-ylmethyl)benzoic Acid;4-((4-METHYLPIPERAZIN-1-YL)METHYL)BENZOIC ACID;4-[(4-methylpiperazin-1-yl)methyl]benzoic acid;4-(4-Methyl-1-piperazinylmethyl)benzoic Acid;4-(4-methylpiperazinomethyl)benzoic acid;Benzoic acid, 4-[(4-methyl-1-piperazinyl)methyl]-;MFCD01632530;Benzoic acid,4-[(4-methyl-1-piperazinyl)methyl]-;ACMC-1BSQT;SCHEMBL65179

    • China Export:

      From 2018.11 to 2019.11, total export volume of 4-(4-Methyl-1-piperazinylmethyl)benzoic acid from China was 35,610,569KG while total export value was $1,117,619,760. The biggest proportion of exporting volume in the last 12 months was 11.77% in 2019.03.

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    Basic Attributes

    • 106261-48-7

    • C13H18N2O2

    • 234.29

    • 234.136826

    • 43.8

    • -1.2

    • ZJUXJQSYXBYFFO-UHFFFAOYSA-N

    • 4

    • 1

    • 0.46

    • 3

    Characteristics

    • 1.2±0.1 g/cm3

    • 181.9±25.1 °C

    • 1.580

    Safety Information

    • 2933599090

    Production Methods

    General procedure: AcOH (100percent) (140 mL, 2.44 ml) was added over 1 h to a flask containing stirred NaBHA suspension of 4-formylbenzoic acid (10.0 g, 67 mmol) in methanol (100 ml) is treated sequentially with 1-methylpiperazine (7.3 g, 73 mmol) and platinum (5percent) on sulfided carbon (1 g). The resulting suspension is then heated at 80° C. and is subjected to a pressure of 5 bar of hydrogen for a period of 20 hrs until the hydrogen uptake is complete. The reaction mixture is cooled to room temperature and filtrated over a pad of Celite. Water (20 ml) is used to rinse the reactor and dissolve the fraction of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid that crystallizes on the walls during the cooling of the reaction mixture. The resulting aqueous solution is filtrated over the pad of Celite employed previously. The combined filtrates are concentrated in vacuo and crystallized in EtOH/H2O 9:1 v/v to give 10.9 g (70percent) of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid as colorless crystals.General procedure: General procedure for saponification: Ester derivative was dissolved in THF (0.8 mol/L) and a water solution of LiOH (3 eq) was added. Mixture was heated to reflux for 4 h. THF was evaporated and impurities were extracted with EtOAc at pH = 12. Aqueous layer was saturated with NaClGeneral procedure: General procedure for saponification: Ester derivative was dissolved in THF (0.8 mol/L) and a water solution of LiOH (3 eq) was added. Mixture was heated to reflux for 4 h. THF was evaporated and impurities were extracted with EtOAc at pH = 12. Aqueous layer was saturated with NaClExample 5 Example 1350 ml of ethanol was added to 155 g (1.547 mol) of N-methylpiperazine. At room temperature (25+/-3° C.), 60 g (0.351 mol) of 4-chloromethylbenzoic acid was added thereto and stirred for 6-7 hours. The reaction was analyzed by HPLC, and then the reaction solution was distilled under reduced pressure to remove ethanol, and 60 ml of 1-butanol was added thereto. The mixture was azeotropically distilled at 70+/-2° C. and concentrated to produce a solid. 600 ml of 2-propanol was added thereto and the mixture was stirred at room temperature (25+/-3° C.) for 30 minutes, stirred under reflux for 15 minutes, and then stirred at room temperature (25+/-3° C.) for 12 hours with slow cooling. The produced precipitate was cooled to 19+/-3° C., stirred for 1 hour and then filtered. The filtrate was washed with 50 ml of cooled 2-propanol and dried in an oven at 60° C., thereby obtaining a white compound of formula (2) (60 g, yield: 72percent, purity: 95percent or higher).HPLC purity: 99.123percent (desmethyl impurity: 0.042percent, starting material 0.42percent).Thin layer chromatography: Methanol-Dichloromethane (7:5), Rf: 0.2.HCL-SALT OF 4- (4-METHYLPIPERAZIN-1-YLMETHYL) benzoic acid methyl ester (1.25 g) was dissolved in potassium hydroxide-methanol solution (0.93 g KOH in 15 ml methanol). Water (0.75 ml) was added and the mixture was refluxed for 1 hour. The reaction mixture was allowed to cool into room temperature and the pH was tuned to 6 with 2 M HC1. The solvent was evaporated and the residue was dried under vacuum. The residue contained 4- (4-METHYLPIPERAZIN-1-YLMETHYL) benzoic acid and inorganic salts. It was used further without purification and the yield of title compound was assumed to be 100percent. 1H NMR (400 MHz, d6-DMSO) 8 : 2.27 (s, 3H), 2.44 (bs, 2H), 3.18-3. 95 (m, 8H), 7.41 (d, 2H, J 8. 0 Hz), 7.89 (d, 2H, J 8. 1 Hz).

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    Material and Products

    China 4-(4-Methyl-1-piperazinylmethyl)benzoic acid Export Data

    Data referenced from General Administration of Customs,P.R.China

    2018.11-2019.11 China - America  4-(4-Methyl-1-piperazinylmethyl)benzoic acid Export Data

    From 2018.11 to 2019.11, total export volume of 4-(4-Methyl-1-piperazinylmethyl)benzoic acid from China to America was 1,696,532KG while total export value was $121,959,783. The biggest proportion of exporting volume in the last 12 months was 14.50% in 2019.01.

    2018.11-2019.11 China 4-(4-Methyl-1-piperazinylmethyl)benzoic acid Export Data

    From 2018.11 to 2019.11, total export volume of 4-(4-Methyl-1-piperazinylmethyl)benzoic acid from China was 35,610,569KG while total export value was $1,117,619,760. The biggest proportion of exporting volume in the last 12 months was 11.77% in 2019.03.

    2018.11-2019.11 TOP10 Purchasing Countries' Export Data of Chinese 4-(4-Methyl-1-piperazinylmethyl)benzoic acid

    From 2018.11 to 2019.11, China has exported 4-(4-Methyl-1-piperazinylmethyl)benzoic acid to 120 countries in total. Country ranks by import volume from high to low is India, Germany, Iran, America, Japan, United Kingdom, Netherlands, Vietnam, Denmark, Singapore. The highest export volume was China to India, accounting for 11.08% of the total volume of China.

    Check Export Data for More Purchasing Countries

    Purchasing Country Export Volume(KG) Export Percentage Export Value($)

    India

    7,110,534

    11.08%

    244,583,865

    Germany

    4,707,416

    7.33%

    83,278,504

    Iran

    2,125,739

    3.31%

    41,079,869

    America

    1,696,532

    2.64%

    121,959,783

    Japan

    1,366,761

    2.13%

    25,494,629

    United Kingdom

    1,172,087

    1.83%

    40,820,094

    Netherlands

    1,108,778

    1.73%

    18,010,932

    Vietnam

    1,025,562

    1.60%

    33,465,278

    Denmark

    980,521

    1.53%

    11,426,872

    Singapore

    924,867

    1.44%

    8,335,186

    Taiwan

    840,441

    1.31%

    14,112,106

    Italy

    835,158

    1.30%

    42,695,379

    Korea

    743,886

    1.16%

    23,688,948

    Brazil

    728,317

    1.13%

    31,427,608

    France

    558,503

    0.87%

    25,360,861

    Pakistan

    552,520

    0.86%

    21,073,608

    Mexico

    543,175

    0.85%

    21,769,279

    Belgium

    528,606

    0.82%

    25,198,184

    Indonesia

    503,682

    0.78%

    12,018,780

    Argentina

    474,987

    0.74%

    21,838,665

    Thailand

    453,914

    0.71%

    11,158,365

    Jordan

    394,981

    0.62%

    6,744,231

    Spain

    391,517

    0.61%

    19,255,579

    Russia

    391,062

    0.61%

    17,191,186

    Bangladesh

    364,491

    0.57%

    15,092,587

    South Africa

    342,454

    0.53%

    8,259,903

    Saudi Arabia

    331,523

    0.52%

    4,090,992

    Colombia

    315,361

    0.49%

    7,645,951

    Turkey

    303,617

    0.47%

    10,717,100

    Switzerland

    288,337

    0.45%

    18,516,252

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