1-Phenylcyclohexylamine compounds

The title compds. are prepd. by treating a quaternary cyclohexylamine salt with a Ph alkali metal compd. or phenylmagnesium halide. Thus, a mixt. of 170 g. piperidine, 220 g. cyclohexanone, and 750 ml. C6H6 is subjected to azeotropic distn. until H2O evolution ceases. The mixt. is then distd. in vacuo to obtain 1-(1-cyclohexenyl)piperidine (I), b8 105 Deg. A mixt. of 190 g. p-MeC6H4SO3H.H2O in 250 ml. PhMe is heated under a H2O trap until anhyd. A soln. of 165 g. I in 500 ml. Et2O is added to this anhyd. soln. at 0-5 Deg, followed by a soln. of 1 mole PhMgBr in 750 ml. Et2O with stirring 30 min. at 5 Deg, the mixt. decompd. by the addn. of excess satd. NH4Cl and concd. NH4OH, the Et2O layer sepd. and dried over K2CO3, the Et2O distd., and the residue distd. in vacuo to yield 1-(1-phenylcyclohexyl)piperidine, b1 135-7 Deg, m. 46-6.5 Deg; HCl salt m. 243-4 Deg; HBr salt m. 225-6 Deg. Similarly prepd. were 1-(1-phenylcyclohexyl)pyrrolidine, b0-14 114-23 Deg, m. 44-5 Deg (HCl salt m. 235-7 Deg), 1-(1-phenylcyclohexyl)-3ethyl-3-methylpyrrolidine, b0-14 126-30 Deg, 1-( 1-phenylcyclohexyl)-3-methylpiperidine, 0-2 123-6 Deg (HCl salt m. 210-11 Deg), 1-(1-phenylcyclohexyl)-4-methylpiperidine, b0-13 128 Deg (HCl salt m. 215-16 Deg), and 1-(1-phenylcyclohexyl)hexamethylenimine' b0-23 137-40 Deg; HCl salt m. 205-6 Deg. Also prepd. were (1-phenylcyclohexyl)ethylpropylamine and (1-phenylcyclohexyl)ethylmethylamine, b0-12 105-8 Deg (HCl salt m. 194-5 Deg). [on SciFinder (R)]