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    Home > Bupropion
    Bupropion structure

    Bupropion

    • CAS No:

      34911-55-2

    • Formula:

      C13H18ClNO

    • Synonyms:

      (+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone;1-dimethylethyl)amino)-1-(3-chlorophenyl)-2-(((+-)-1-propanon;alpha-(tert-butylamino)-m-chloropropiophenone;Wellbutrin1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino)-1-propamone;BUPROPION HCL;DL-1-(3-CHLOROPHENYL)-2-[(1,1-DIMETHYLETHYL)AMINO]-1-PROPANONE HYDROCHLORIDE;AMFEBUTAMONE;AMFEBUTAMONE HCL

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    Basic Attributes

    • 34911-55-2

    • C13H18ClNO

    • 239.74

    • 239.10800

    • 29.10000

    • 3.69020

    Characteristics

    • white solid

    • 1.066g/cm3

    • 233-234°C

    • bp.005 52°

    • 156.3ºC

    • ethanol: 193 mg/mL solutions may be stored for several days at 4 °C.

    Safety Information

    • IRRITANT

    • 3

    • 22

    • 36

    • UG8858000

    • Xn

    Product Usage

    vasoconstrictor;non-selective agonist of all adrenergic receptors

    Production Methods

    Under stirring and cooling, to a solution of ethylmagnesium bromide (2L, 3mol/L), add a solution of o-chlorobenzeneacetonitrile (688g, 5mol) dissolved in ether (2.5L) within 40min. Heat under mild reflux for 5h. The reaction solution was hydrolyzed with cold dilute hydrochloric acid. After distilling off the ether, the remaining aqueous solution was heated at 90°C for 1 h. After cooling, put in seed crystals. The solid was collected by filtration, washed with cold water, and then recrystallized from methanol to obtain 750 g of o-chlorophenylacetone, melting point 39-40°C. Dissolve o-chlorophenylacetone (698g, 4.15mmo1) in dichloromethane (3L). The solution was stirred with activated carbon and magnesium sulfate for 2h and filtered. A solution of 662 g (4.15mol) of bromine in dichloromethane (1 L) was added with stirring. After the bromine color completely disappeared, the solvent was concentrated in vacuo to remove the solvent. The remaining oil was o-chloro-α-bromophenylacetone, which was used directly in the next step without purification. The oily residue obtained above was dissolved in acetonitrile (1300 ml), and a solution of tert-butylamine (733 g) in acetonitrile (1300 ml) was added below 32°C. After standing overnight, 4200 ml of water and 2700 ml of ether were added for distribution. The water layer was extracted with 1300 ml of ether. After the ether layers were combined, 4200 ml of water was added, and hydrochloric acid was added until the Ph value of the water layer was 9. The separated aqueous layer was washed with 500 ml of ether. The ether layers were combined, and 560 g of ice and 324 ml of concentrated hydrochloric acid were added and stirred together. The ether layer was separated and washed with 200 ml of water and 50 ml of concentrated hydrochloric acid. The last two acid layers were combined, concentrated in vacuo until crystallization occurred, and cooled to 5°C. Filter, wash with acetone, and recrystallize with a mixture of 3L isopropyl alcohol and 800ml absolute ethanol. Analytical and spectrally pure DL-bupropion hydrochloride was obtained, melting point 233~234℃.

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