Hydrochloric Acid → HCID 86635427, compound

Participants

Reaction Steps

To 4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (Ex. 3b, 21 g, 50 mmol) in a 250 mL round bottom flask was added 100 mL of a 4 N HCl in dioxane. The mixture was stirred at room temperature for 5 h and concentrated under reduced pressure to about 25 mL. The solid was collected through filtration, washed with Ethyl acetate/hexanes (1:2 v/v, 50 mL), and dried under high vacuum to afford 2,6-di-tert-butyl-4-(piperidin-4-ylsulfanyl)-phenol hydrochloride as a white solid (16 g, 97%). 1H NMR (400 MHz, CD3OD): δ 7.26 (s, 2H), 3.35 (m, 2H), 3.10 (m, 1H), 3.00 (m, 2H), 2.11 (m, 2H), 1.68 (m, 2H), 1.37 (s, 18H). ESI/CI-MS m/z 322 ([M+H]+), 320 ([M−H]−). HRMS (ESI) Calcd. for C19H32ClNOS: 321.2126 (M+). Found: 321.2127. Anal. Calcd. for C19H32ClNOS, C, 63.75; H, 9.01; N, 3.91; S, 8.96. Found: C, 63.43; H, 9.08; N, 3.94; S, 8.72.

Provenance & Evidence