Triethylamine → trans-N-[2-(Dimethylamino)cyclohexyl]alpha,alpha,alpha-trifluoro-p-toluamide

Participants

Reaction Steps

The titled amide was prepared according to general procedure B using p-trifluoromethyl-benzoyl chloride (4.17 g.; 0.02 mole), N,N-dimethylcyclohexane-1,2-diamine (2.84 g.; 0.02 mole) and triethylamine (2.02 g., 0.02 mole). The crude solid was crystallized from ether to give 4.766 g. (77% yield) of colorless needles, m.p. 141°-142°, raised to 141.5°-142.5° on recrystallization. uv λmax 222 nm (ε 11,450), sh 245 (5,550); sh 260 (3,400); sh 276 (1.750). ir NH 3310; =CH 3030; N-alkyl 2770, 2740; C=O 1635; C=O 1575, 1510; amide II 1550; CF3 /ether 1330, 1190, 1165, 1130, 1105, 1065, 1020; aromatic 860; nmr in CDCl3 at 100 MHz was in accord. Mass spectrum M+ 314.

Provenance & Evidence