Benzo(B)Thiophene → HCID 15337059, compound

Participants

Reaction Steps

Benzothiophene (10 g, 0.07 mol) was dissolved in tetrahydrofuran (150 ml) and cooled to -10° C. (ice/methanol). Butyl lithium (33 ml of 2.5M in hexane, 0.077 mol) was added dropwise and the reaction mixture warmed to room temperature over one hour. Following addition of N-benzyl piperidone (9.16 ml, 0.07 mol) at -40°, the reaction was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the crude product purified by flash chromatography eluting with 20% and 30% ethyl acetate in petroleum ether to give an orange/red solid. Recrystallisation from ether afforded the title compound as a pale yellow solid (16.87g, 75%); δH (CDCl3), 1.96 (2H, m, NCH2 CH2), 1.99 (1H, s, OH), 2.25 (2H, t of d, J 13.5Hz, J 4.4Hz, NCH2CH2), 2.51 (2H, t of d, J 11.6Hz, J 2.46Hz, NCH2 CH2), 2.76 (2H, m, NCH2CH2), 3.57 (2H, s, NCH2, Ar), 7.30 (8H, m, ArH), 7.70 (1H, d, J 7Hz, ArH), 7.79 (1H, d, J 7.6Hz, ArH). m/z (ES+) 324 (M+1)+.

Provenance & Evidence