Triethylamine → trans-N-[2-(Dimethylamino)cyclohexyl]-p-nitro-benzamide

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Reaction Steps

This titled amide was prepared from the trans-diamine and 4-nitrobenzoylchloride according to general procedure B using p-nitrobnzoylchloride (1.86 g.; 0.01 mole), the diamine (1.42 g) 0.01 mole) and triethylamine (1.01 g.; 0.01 mole). The crude oil was crystallized from ether-petroleum ether (30°-60°); 2.232 g. (77% yield) of yellow needles, m.p. 103°-104°. The analytical sample melted at 102°-103°. uv sh ;b 215 nm (λ 2,000); εmax 266 (11,800). ir NH 3380, 3320; N-alkyl 2780; C=0 1645; C=C 1605, 1595; amide II/NO2 /C=C 1535, 1525, 1485, 1350; aromatic 870, 845, 720, nmr in CDCl3 and 100 MHz was in accord. Mass spectrum M+ 291.

Provenance & Evidence