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ChemicalBook CAS DataBase List Tamoxifen citrate
54965-24-1

Tamoxifen citrate synthesis

9synthesis methods
Tamoxifen, sold under the brand name Nolvadex among others, is a medication that is used to prevent breast cancer in women and treat breast cancer in women and men. Tamoxifen citrate can be synthesized by using simple and accessible 4-hydroxybenzophenone as a raw material, carrying out coupling reaction and alkylation reaction to obtain a crude product 2-[4-(1,2-diphenyl1-butenyl)-phenoxy]-N,N-dimethylethylamine; directly carrying out isomerization reaction on the crude product, carrying out simple purification, and salifying with citric acid to obtain the high-purity tamoxifen citrate.
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Yield:54965-24-1 91.3%

Reaction Conditions:

in propan-2-one at 40 - 70; for 2 h;Industrial scale;Temperature;

Steps:

1.4; 2.4; 3.4 (4) Salt-forming reaction:

11.53kg of tamoxifen free base and 59kg of acetone were added to the dissolving kettle, and the temperature was raised to 40°C.Heat preservation and dissolving for 20min until clarification, the feed liquid is suction filtered through a two-stage filter to a salt-forming kettle;7.01kg of citric acid and 38kg of acetone were added to another dissolving kettle, and the temperature was raised to 40°C,Heat preservation and dissolving for 20min until clarification, the feed liquid is suction filtered through a two-stage filter to a salt-forming kettle;The temperature of the salt-forming kettle was controlled at 40 °C, kept for 30 minutes, and then cooled to below 20 °C.The material was discharged to a centrifuge for centrifugation, the filter cake was taken out, and dried at 70°C for 2 hours.Use a 40-mesh sieve of a universal pulverizer to granulate to obtain pure tamoxifen citrate,It is a white or off-white powder crystal, the melting point is 142-148 ° C, and it decomposes at the same time when it is melted.Isomer < 0.05%, other impurities and < 0.5%, calculated as dry product, (Z) C26H29NO·C6H8O7 content is more than 99.5%, weighing 16.0kg,Yield 91.3%. The pure tamoxifen citrate obtained in this example is detected,The chromatogram is shown in Figure 1, and the infrared spectrum is shown in Figure 2.

References:

CN114133334,2022,A Location in patent:Paragraph 0059; 0066-0067; 0068; 0075-0076; 0077; 0084-0085

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