Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Cl.[OH-].[Na+].[OH-].C[N+](C)(C)CC1C=CC=CC=1>C1C=CC=CC=1>[Cl:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][N:7]1[CH2:8][CH2:9][C:10]2[S:2][CH:3]=[CH:4][C:5]=2[CH2:6]1To a solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (580 mg, 3.3 mmol) and 2-chlorobenzyl chloride (640 mg, 3.9 mmol) in benzene (5.0 ml) were added an aqueous 5M NaOH solution (5 ml), and trimethylbenzyl ammonium hydroxide (100 mg of 40% methanol solution). The mixture was stirred for 40 hours at room temperature. The reaction mixture was allowed to stand, thereby separating an aqueous layer from an organic layer The organic layer was washed with water and then with saturated NaCl solution, dried (over MgSO4) and concentrated. The residue was purified by silica gel column chromatography to prepare 650 mg (yield 74.7%) of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine as an oily product, b.p. 155.0°-158.0° C. (1.5 mmHg). This pyridine was dissolved in hydrogen chloride saturated ethyl alcohol (5 ml) and the solution was then concentrated and cooled. The precipitated hydrochloride was filtered off and dried. The yield 420 mg (42.4%), m.p. 190° C.
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