Reaktion #409773

Reaktionsgleichung

sodium cyanoborohydride

hydrogen 2

3-methyl-3-(4-chlorophenyl)cinnamonitrile

3-methyl-3-(4-chlorophenyl)propylamine

3′-methoxyacetophenone

4-chloroacetophenone

→

N-[3-methyl-3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

Lösungsmittel

acetic acid

Reaktionsbedingungen

Vorschrift

In a similar fashion, 4-chloroacetophenone was used to prepare 3-methyl-3-(4-chlorophenyl)cinnamonitrile. The nitrile was catalytically reduced (palladium hydroxide, acetic acid, 60 p.s.i. hydrogen 2 hr) to generate 3-methyl-3-(4-chlorophenyl)propylamine. An equal molar amount of the amine, 3′-methoxyacetophenone and 1.25 molar equivalents titanium(IV) isopropoxide were mixed 4 hr at rt and the intermediate imine treated with an ethanolic sodium cyanoborohydride (5 ml of 1 M, 5 mmol). Work-up and chromatography afforded N-[3-methyl-3-(4-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 5B/5C as an oil; m/z (rel. int.) 317 (M+, 12), 302 (74), 210 (2), 182 (4), 164 (12), 135 (100), 121 (25), 103 (40), 91 (19), 77 (28).

Quelle