Water → HCID 68183338, compound

Participants

Reaction Steps

In a 250 mL round bottomed flask was placed 4-[4-(4-chlorophenyl)-4,5,6,7-tetrahydro-1-benzothien-2-yl]pyridine hydrochloride (2.1 g, 5.8 mmol) and then suspended in 1 M of Sodium hydroxide in water (50 mL, 50 mmol). To the mixture was added ethyl acetate (50 mL) and the mixture was vigorously stirred for 30 min at rt. The aqueous phase was extracted with EtOAc (50 mL×2) and the combined organic phase was dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (1.85 g; 98%) as a brown syrup, which was spontaneously solidified by keeping on standing at rt for 3 h. 1H NMR (300 MHz, d1-chloroform) δ: 8.51 (d, 2H), 7.26-7.35 (m, 4H), 7.09 (d, 2H), 6.91 (s, 1H), 3.98 (t, 1H), 2.90 (t, 2H), 1.71-2.21 (m, 6H).

Provenance & Evidence