Hydrochloric Acid → HCID 68108770, compound

Participants

Reaction Steps

To a solution of the product of step C (190 mg, 0.41 mmol) in tetrahydrofuran (10 mL) was added conc. hydrochloric acid (1.2 mL, 12.34 mmol) at ambient temperature. After 15 h, the reaction was basified with 10% NaOH solution and extracted with dichloromethane. The organic layer was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, 95:5 dichloromethane/methanol) to provide the free base which was converted directly to the hydrochloride salt by dissolving in methanol and treating with 1.25 M HCl in methanol. Concentration in vacuo afforded 6-chloro-4-methyl-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (70 mg, 48%, AUC HPLC 96.8%) as a white solid: mp 291-292° C. dec; 1H NMR (DMSO-d6, 400 MHz) δ 9.72 (br s, 2H), 8.43 (s, 1H), 8.09-7.99 (m, 3H), 7.74-7.59 (m, 3H), 4.49-4.28 (m, 2H), 3.71-3.44 (m, 2H), 3.19-3.11 (m, 1H), 1.35 (d, J=4.8 Hz, 3H); APCI MS m/z 362 [M+H]+.

Provenance & Evidence