[C:1]([C:3]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[CH:4]=1)#[CH:2].C=O.[CH3:21][NH:22][CH3:23].[CH3:24]S(O)(=O)=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O1CCOCC1>[CH3:21][N:22]([CH2:24][C:2]#[C:1][C:3]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[CH:4]=1)[CH3:23]A solution of 5.1 g. of 10-ethynyl-8-chloro-dibenzo[b,f]-thiepin in 40 ml. of absolute dioxane is treated with 630 mg. of paraformaldehyde, 4.5 ml. of a 6-M solution of dimethylamine is dioxane and 200 mg. of copper (II) acetate. The mixture is heated at 100° C. in a well-sealed flask for 2 hours. After cooling, the mixture is poured onto ice and then acidified with 3-N methanesulfonic acid. The neutral products are removed by extraction with ether. The aqueous phase is made alkaline with ammonia. By extraction with ether, there is obtained N,N-dimethyl-3-[8-chloro-dibenzo[b,f]thiepin-10-yl]-2-propynylamine, which melts at 118°-120° C. after recrystallization from hexane. The maleate melts at 178°-180° C.
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