2-Chlorobenzaldehyde → rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 8.98 g (86.33 mmole) sodium bisulfite in water (27 mL), o-chlorobenzaldehyde 12.4 g (86.33 mmole) was added resulting in a white precipitate. To the precipitate, 15 g (0.107 moles) of 6,7-dihydro-4H-thieno[3,2-c]pyridine was added, followed by addition of 4.4 g (89.7 mmoles) NaCN (dissolved in 15 mL water). The reaction mixture was heated at 40-50° C. for 6 hrs and was quenched by pouring in water (50 mL). The mixture was extracted with 2×100 mL of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The yield of the title product is 24 g (97%).

Provenance & Evidence