p-Toluenesulfonic acid → HCID 86736411, compound

Participants

Reaction Steps

A solution of trans-N-benzyl-N',N'-dimethyl-1,2-cyclohexanediamine (9.29 g., 0.04 mole) prepared as in Procedure IV, but using benzylamine instead of benzylmethylamine, in 40 ml. of formic acid is refluxed 20 hr., and poured into 200 g. of ice. It is basified with 15% NaOH and extracted well with ether. The extract is washed with H2O and with saturated salt solution, is dried (MgSO4) and evaporated. The residue is converted with 2 mole of p-TSA in ether. The resulting gum is crystallized from MeOH-ether to give 13.64 g. of title compound, m.p. 201°-201.5°. The analytical sample melts at 202°-203°. uv:sh 210 nm (ε 27,850); sh 222 (25,600); sh 227 (12,350); sh 243 (302); sh 248 (375); λmax 254 (472); 258 (556); 261 (562); 268 (399); sh 272 (175). ir:NH 2720, 2560; C=O 1670, 1650; C=C 1600, 1495; SO3 /other 1225, 1170, 1120, 1030, 1010, 815, 705, 685. nmr in D2O (100 MHz) is in accord. Mass spectrum M+ 260.

Provenance & Evidence