[NH2:1][CH2:2][CH:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[S:6][CH2:5][CH2:4]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CO.C([BH3-])#N.[Na+]>[CH2:16]([NH:1][CH2:2][CH:3]1[C:15]2[C:7](=[N:8][C:9]3[C:14]=2[CH2:13][CH:12]=[CH:11][CH:10]=3)[S:6][CH2:5][CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1To a solution of 4-aminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (150 mg) in methanol (5 ml) are added a solution of benzaldehyde (76 mg) in methanol (1.5 ml) and sodium cyanoborohydride (132 mg). The mixture is adjusted to pH 7 with a solution of hydrochloride in methanol, stirred at room temperature for 1 hour and evaporated to remove the solvent. The residue is dissolved in ether, washed with a 10% aqueous solution of sodium hydroxide and a saline solution, dried and evaporated to give the title compound (210 mg).
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