Ethanethiol → HCID 22907018, compound

Participants

Reaction Steps

The AlCl3 (1.9 g, 14 mmol) was stirred in 50 mL of DCE at 0° C., ethanethiol (1.5 mL, 20 mmol) was added, and the mixture stirred for 15 min. The 2-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-(4-fluorophenyl)pyridine (1 g, 2 mmol) in 25 mL DCE was added dropwise to the reaction mixture and stirred for 2 h as it was allowed to come to rt, then quenched with 25 mL THF at 0° C., followed by 25 mL 1N HCl and worked up. The crude product was triturated with Et2O, filtered, and dried in vacuo to give 0.86 g (91% yield) of white solid: mp 194°-195° C.; 1H NMR (CDCl3) d 1.63-167 (comp, 6H, piperidine), 2.59 (bs, 4H, piperidine), 2.81-2.84 (t, 2H, J=5 Hz, CH2N), 4.12-4.15 (t, 2H, J=5 Hz, OCH2), 6.64-6.70 (m, 4H, ArH), 7.00-7.03 (d, 2H, J=8 Hz, ArH), 7.12-7.18 (m, 2H, ArH), 7.37-7.40 (d, 2H, J=8 Hz, ArH), 7.61-7.67 (m, 2H, ArH), 8.08-8.12 (m, 2H, ArH); MS (FD) 468 (M+). Anal. Calcd for C30H29N2O2F: C, 76.90; H, 6.24; N, 5.98. Found: C, 77.13; H, 6.36; N, 5.86.

Provenance & Evidence