N-Allylaniline → 3-(4-Chlorophenyl)-3-(1H-imidazol-1-ylmethyl)-2-methyl-5-[(phenylamino)methyl]isoxazolidine

Beteiligte Stoffe

Reaktionsschritte

Derivative 3 (R1 =4-Cl, R2 =R3 =H) is obtained by a procedure similar to that described in Example 1 by reacting 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide (1: R1 =4-Cl) with N-phenyl-2-propen-1-amine (2: R2 =R3 =H). The product cis-/trans-diastereometric mixture is flash-chromatographed on neutral silica gel using chloroform-methanol (97:3 by volume) as eluent. Isomer A has a melting point of 159°-160° C. (ethyl acetate). Anal. Calcd for C21H23ClN4O: C, 65.87; H, 6.05; N, 14.63; Cl, 9.26. Found: C, 65.77; H, 6.20; N, 14.42; Cl, 9.48. Isomer B has a melting point of 172°-173° C. (ethyl acetate).

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