METHOD OF SYNTHESIS OF (Z)-1-[4-(2-DIMETHYLAMINOETHOXY)PHENYL]-1,2- DIPHENYLBUT-1-EN Russian patent published in 1994 - IPC

FIELD: organic chemistry, substituted amines. SUBSTANCE: product: (Z)-1-[4-(2-dimethylaminoethoxy)phenyl] -1,2-diphenylbut-1-en. synthesis is carried out by reduction cross-linking of 4-hydroxybenzophenone and propiophenone in the presence of low-valent titanium compound (obtained in situ from TiCl₄ and zinc) in the medium of tetrahydrofuran, which is distilled off azeotrolically after reaction. Obtained mixture then is extracted with benzene, treated with concentrated solution of NH₃ and after removal inorganic bases benzene solution is treated successively with aqueous solution of NaOH and dimethylaminoethyl chloride chlorohydrate. Then boiling with distillation of aqueous azeotrope is carried out following by washing with water and evaporation until dry. Prepared oil is dissolved in organic solvent - isopropanol or acetone, treated with 20-30% aqueous solution of sulfuric acid. The end product is isolated in the form of hydrosulfate, which then is converted to the base. Synthesized compound is a semiproduct for synthesis of tamoxifen-citrate, which is antitumor drug. EFFECT: increased yield of Z-isomer (up to 44.23%), content is 99%, simplified process.