C=O.[CH3:3]S(O)(=O)=O.[Cl:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][NH:12][CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.[OH-].[Na+].Cl>CN(C)C=O.C(O)C>[ClH:8].[Cl:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][N:12]1[CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][C:19]=2[CH2:3]1
To 2.25 g (0.075 M) paraformaldehyde suspended in 20 ml dimethylformamide are added 9.61 g (0.1 M) methanesulfonic acid. The medium being at a temperature of 72° C., 13 g (0.05 M) N-(2-chloro-benzyl)-2-(2-thienyl)ethylamine dissolved in 5 ml dimethylformamide are added over 2 minutes. The temperature of the reaction medium reaches 90° C. The reaction medium is then cooled to 20° C. and poured over 50 ml 4N sodium hydroxide. The material is extracted with 1×30 ml and then 1×20 ml methylene chloride. The organic phases are combined, dried over sodium sulfate and evaporated, to give an oil which is taken up into 30 ml ethanol in which are dissolved 0.15 mole gaseous hydrochloric acid. After partial evaporation of the ethanol, the desired product precipitates out. It is filtered, washed with acetone and dried, to give 11.35 g 5-(2-chloro-benzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (Yield: 75.6%).
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