[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.Cl[CH2:18]OC.O>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][C:8]2[S:9][CH:10]=[CH:11][C:12]=2[CH2:18]1To a solution of 50.8 g (0.2 M) N-(2-chloro-benzyl)-2-(2-thienyl)-ethylamine in 70 ml dimethylformamide heated at 60° C. is added, over 7 minutes, 22.7 g (0.24 M) chloromethylmethylether. The temperature of the reaction medium is maintained at 60° C. throughout the addition step by cooling with water. Thirty minutes after completion of the chloromethylmethylether addition, the medium is cooled to 20° C. The desired product, which has precipitated out, is filtered and washed with 2×70 ml acetone, to give 45.1 g 5-(2-chloro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine hydrochloride (Yield: 75%).
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