[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:13][CH2:12][CH2:11][CH2:10][S:9]2)=[CH:4][CH:3]=1.O1CCCC1.C([Li])CCC.[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([CH2:29][CH2:30][N:31]([CH2:33][CH:34]([CH3:37])[CH2:35]Cl)[CH3:32])=[CH:27][CH:26]=1>CCCCCC.O>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH:34]([CH3:37])[CH2:35][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[S:9][CH2:10][CH2:11][CH2:12][S:13]2)=[CH:38][CH:39]=12.77 g (0.012 mol) of 2-(4-chlorophenyl)-m-dithiane and 10 ml of abs. tetrahydrofuran were cooled to -70° in a sulphonation flask while gassing with argon and treated with 7.50 ml (0.012 mol) of butyllithium in hexane. Thereupon, the mixture was stirred at -20° for 2 hours. A solution of 2.50 g (0.0096 mol) of rac-4-chloro-N-(3-chloro-2-methylpropyl)-N-methylphenethylamine in abs. tetrahydrofuran was added dropwise thereto at -70° within 15 minutes, whereupon the mixture was left to stand at -20° for 18 hours and at room temperature for 3 hours. The reaction solution was then poured into water and extracted three times with ether. The ethereal extracts were dried over magnesium sulphate and evaporated. The residual oil was chromatographed on silica gel with toluene-hexane (1:1). After evaporating the solvent and warming the residue at 50° for 18 hours under reduced pressure there was obtained rac-N-(4-chlorophenethyl)-2-(4-chlorophenyl)-β,N-dimethyl-m-dithiane-2-propanamine as a viscous oil.
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