Potassium Carbonate → HCID 11121342, compound

Participants

Reaction Steps

4-(Benzothiophen-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (250 mg, 0.99 mmol) was dissolved in DMF (5 ml), potassium carbonate (412 mg, 2.9 mmol) added, and the reaction mixture stirred at room temperature for 10 minutes. 4-Chlorobenzyl bromide (306 mg, 1.5 mmol) was added and the resulting reaction mixture stirred at room temperature overnight. After dilution with water (50 ml), the product was extracted into ethyl acetate (3×40 ml). The combined organic layers were washed with brine (100 ml), dried (MgSO4) and concentrated. The crude product was triturated with methanol to yield a pale brown solid. Recrystallisation from hot dichloromethane and methanol gave the title compound as a pale yellow solid (60 mg, 18%); (Found: C, 70.33; H, 5.20; N, 4.16. C20H18 ClNS requires C, 70.68; H, 5.34; N, 4.12%); δH (CDCl3), 2.64 (2H, m, NCH2CH2), 2.72 (2H, m, NCH2CH2), 3.18 (2H, m, NCH2CH2), 3.61 (2H, s, NCH2Ar), 6.18 (1H, m, NCH2CH2), 7.12 (1H, s, ArH), 7.28 (6H, m, ArH), 7.66 (1H, d of d, J 6Hz, J 2Hz, ArH), 7.74 (1H, d of d, J 6.7Hz, J 2Hz, ArH). m/z (ES+) 340 (M+1)+.

Provenance & Evidence