HCID 15337059, compound → HCID 9861313, compound

Participants

Reaction Steps

4-(Benzothiophen-2-yl)-1-benzyl-4-hydroxypiperidine (4.5 g, 0.01 mol) was dissolved in trifluoroacetic acid (50 ml) and stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between aqueous saturated potassium carbonate solution and dichloromethane (3×100 ml). The combined organic layers were washed with brine (200 ml), dried (MgSO4) and concentrated. The crude product was purified by flash chromatography eluting with 10% ethyl acetate in petroleum ether. Concentration of the appropriate fractions gave the title compound as a pale yellow solid (3.5 g, 82%); δH (CDCl3), 2.63 (2H, m, NCH2CH2), 2.73 (2H, m, NCH2 CH2), 3.19 (2H, m, NCH2CH2), 3.64 (2H, s, NCH2Ar), 6.19 (1H, m, NCH2CH), 7.11 (1H, s, ArH), 7.31 (7H, m, ArH), 7.65 (1H, d of d, J 6.4Hz, J 1.9Hz, ArH), 7.72 (1H, d of d, J 6.9Hz, J 1.8Hz, ArH). m/z (ES+) 306 (M+1)+.

Provenance & Evidence