Hydrochloric Acid → HCID 11983234, compound

Participants

Reaction Steps

[2-(Benzo[b]furan-3-ylsulfanyl)-benzyl]-methyl-carbamic acid tert-butyl ester (9.2 g, 24.9 mmol) is dissolved in methanol (75 mL) and diethyl ether saturated with hydrochloric acid (75 mL) is added. The mixture is stirred at ambient temperature for 1 hour and then concentrated in vacuo. Water (50 mL) is added to the remanence and the mixture is basified by addition of aqueous ammonia (conc.). The aqueous fraction is extracted with ethyl acetate (3×100 mL). The combined organic fractions are dried (MgSO4) and concentrated in vacuo. The product is purified by preparative HPLC or by silica gel chromatography eluting with ethyl acetate-triethyl amine (25:1) to furnish the title compound as an oil. This oil can be redissolved in ethyl acetate (75 mL). Diethyl ether saturated with hydrochloric acid can be added hereto until pH 2. The precipitated material can then be filtered off and dried in vacuo to give 6.9 g (91%) of [2-(benzo[b]furan-3-ylsulfanyl)-benzyl]-methyl-amine hydrochloride as a white crystalline material.

Provenance & Evidence