Ethanethiol → HCID 12992516, compound

Participants

Reaction Steps

To a solution of the product from Example 18, Step 2 (63 mg, 0.21 mmol) and 4-(2-Piperidin-1-yl-ethoxy)-benzoyl chloride (1.38 mL, 0.25 mmol) in 1 mL of methylene chloride was added AlCl3 (212 mg, 1.6 mmol) and the reaction was stirred at room temperature for 3 hrs. When acylation was complete, to demethylate, ethanethiol (0.069 mL, 0.93 mmol) was added dropwise and the reaction stirred for a further 1.5 hrs. The reaction was cooled to 0° C. and quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with 10% MeOH/methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using 2% MeOH/methylene chloride to 4% MeOH/methylene chloride as the gradient eluant to obtain the title product.

Provenance & Evidence