Aminoprofen

Aminoprofen, an amide of ibuprofen, is a topical anti-arthritic with analgesic properties. It is comparable to methyl salicylate in the carrageenan-induced paw edema and croton oil ear edema models, and is reported to be a superior analgesic.

ChEBI: Mabuprofen is a monoterpenoid.

Method 1: Dissolve ibuprofen in benzene, and slowly add thionyl chloride dropwise with stirring. After adding, continue to stir, then reflux. The remaining thionyl chloride and benzene were evaporated under reduced pressure below 40°C. Then add benzene to the residue, stir well, and then concentrate to dryness under reduced pressure to obtain 2-(4-isobutylphenyl) propionyl chloride as a yellow oil. Mix anhydrous potassium carbonate and 2-aminoethanol and cool to 5°C. Slowly add 2-(4-isobutylphenyl) propionyl chloride dropwise with stirring, maintaining the temperature not exceeding 20°C. After adding, continue to stir, and then react at 75°C. Cool, add water and extract with ether. The extract was washed twice with water, 20% sodium hydroxide solution, and 4mol/L hydrochloric acid in order to remove unreacted ibuprofen and aminoethanol, and finally washed with water until it was neutral and dried. Concentrate, add aminprofen seed crystals to the remaining oily viscous material. The product solidified into white waxy crystals of Aminprofen with a melting point of 36～38°C. Method 2: 100g ibuprofen and 400ml aminoethanol are refluxed for 24h. Add ether and brine, separate the organic layer and treat to obtain ambuprofen. Or ibuprofen and aminoethanol in carbon tetrachloride under the action of triethylamine and triphenylphosphine. Aminprofen can also be obtained by reaction at room temperature.

Anti-inflammatory analgesic, its effect is better than ibuprofen, no irritation to the gastrointestinal tract, well tolerated.