Thiophene → 1,2,3,4-Tetrahydro-2-[(4-phenoxy-phenyl)methyl]benzothieno[2,3-c]pyridine

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Reaction Steps

A mixture of 1,2,3,4-tetrahydro-[1]benzothieno[2,3-c]pyridine hydrochloride (1:1) (0.01 mol) and phenoxybenzaldehyde (0.01 mol) in methanol (150 ml) was hydrogenated at 50° C. with Pd/C 10% (1 g) as a catalyst in the presence of potassium acetate (2 g) and thiophene 4% (1 ml). After uptake of H2 (1 equiv), the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from CH3CN, filtered off and dried. This fraction (3 g) was stirred in water with a little NH4OH, and this mixture was extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered and the solvent evaporated. The residue was crystallized from CH3CN, filtered off and dried, yielding 2.7 g of 1,2,3,4-tetrahydro-2-[(4-phenoxy-phenyl)methyl]benzothieno[2,3-c]pyridine (compound 34).

Provenance & Evidence