Ethanethiol → HCID 22907022, compound

Participants

Reaction Steps

The AlCl3 (1.2 g, 9 mmol) was stirred in 30 mL of DCE at 0° C., ethanethiol (1 mL, 14 mmol) was added, and the mixture stirred for 15 min. The 2-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-methylpyridine (0.5 g, 1.2 mmol) in 20 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 free base gave a very clean NMR, but the elemental analysis was low for carbon and hydrogen, so it was taken up in 50 mL hot acetone, citric acid H2O (0.2 g, 0.9 mmol) was added, then heated 10 min, concentrated, triturated with Et2O, filtered, and dried in vacuo to give 0.38 g (72 % yield) of product as the citrate salt: mp 90°-100° C.; 1H NMR (CDCl3) (free base) d 1.34-1.66 (comp, 6H, piperidine), 2.42-2.65 (comp, 7H, pyr-CH3 and piperidine), 2.70-2.79 (m, 2H, CH2 N), 3.95-4.10 (m, 2H, OCH2), 6.50-6.59 (m, 4H, ArH), 6.76-6.85 (d, 2H, J=8 Hz, ArH), 6.98-7.05 (d, 1H, J=8 Hz, ArH), 7.10-7.21 (m, 2H, ArH), 7.41-7.50 (d, 1H, J=8 Hz, ArH); MS(FAB) 398 [M+i]+Anal. Calcd for C25H28N2O2 ·C6H8O7 : C, 64.13; H, 6.25; N, 4.82. Found: C, 63.99; H, 6.36; N, 4.58.

Provenance & Evidence