CN(C)C[CH2:4][CH:5]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.C([Li])CCC.[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29]CCl>CCOCC.CCCCCC>[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:4][CH:5]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2A solution of 3.10 g 11H-dibenzo(b,e)-1,4-dithiepin (of example 14, reference given) in 50 ml of ether was stirred and treated dropwise with 10 ml of 15% n-butyllithium solution in hexane for 15 minutes in a nitrogen atmosphere. The mixture was stirred for another 30 minutes at room temperature. It was then treated dropwise with 10 ml of 3-dimethylaminopropyl chloride, the mixture stirred for 4 hours and washed with water. The basic product was then extracted with dilute hydrochloric acid, the acid layer made alkaline with aqueous ammonia and the base extracted with ether. Processing of the extract yielded 3.7 g for oily base which was chromatographed on a column of 200 g neutral of aluminium oxide (activity II). A small amount of less polar impurities was initially eluted with benzene which then eluted 2.89 g of a homogeneous oily base which was converted by neutralization with oxalic acid to the hydrogen oxalate, m.p. 181°-182° C. (ethanol).
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