hydropyridine derivative (22), however, extension of this argument to the 7-membered tetrahydroazepine (23) cannot be made due to the variability in the pretreatment averages.
Experimental SectionAll melting points were determined on a Thomas-Hoover capillary melting point apparatus and are cor. Where analyses are indicated only by symbols of the elements, anal, results obtained for those elements were within ±0.4% of the theor values. Nmr and ir spectra were recorded for all the compds and are consistent with assigned structures.2-(3,4-Dimethylphenyl)amino-l-pyrroline HCl ( 16).-A soln of POClg (31.0 g, 0.2 mole) in 20 ml of PhMe was added in dropwise amts to a stirred, cooled (10°) soln of 2-pyrrolidinone (4) (34.0 g, 0.4 mole) in 20 ml of PhMe. The temp during the addn (20 min) was maintained at 10-15°, then allowed to return to room temp for 3 hr. A soln of 3,4-xylidene (24.2 g, 0.2 mole) in 20 ml of PhMe was added, and the mixt was heated to reflux overnight. It was cooled to room temp, and the PhMe layer was decanted. The residue was dissolved in 150 ml of H20 and extd with 150 ml of CeH«. NaOH (100 ml, 6 N) was then added to the aq layer. The resultant alkaline mixt was cooled and 27.65 g (73%) of a light tan solid collected, mp 150.5-152.5°. Recrystn from MeCN yielded light tan crystals, mp 151-153°. Anal. (Ci.2Hj.eN2) C, , N.The HC1 salt was prepd in Et20 by addn of Et20 satd with dry HC1. Recrystn from EtOH-EtaO gave a colorless powder, mp 222-223°. Anal. (Ci2Hi«N2-HC1) C, , N, Cl.2-(2,6-Dichlorophenyl)amino-3,4,5,6-tetrahydropyridineHCl ( 22).-A cold (-10°), stirred soln of cyclopentanone oxime (9.9 g, 0.1 mole), 2.5 N KOH (50 ml), and Me2CO (10 ml) was treated dropwise with PhS02Cl (18 g, 0.1 mole). The temp of the resultant mixt was maintained at -10°for 1 hr. The reac-
