Hydrochloric Acid → 5-(4-(2-(Piperidin-1-yl)ethoxy)phenoxy)-6-(thiophen-2-yl)naphthalen-2-ol hydrochloride

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-(2-(4-(6-methoxy-2-(thiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine (100 mg, 0.22 mmol) in dichloromethane and treat with HCl (1M in ether; 220 μL, 0.22 mmol). Concentrate in vacuo to give a yellow solid and add dichloromethane (7.3 mL). Cool the resulting solution to 0° C. and add boron tribromide (1M in dichloromethane; 870 μL, 0.87 mmol). Stir the resulting mixture at 0° C. for 2.5 hours. Quench the mixture with saturated aqueous sodium bicarbonate and allow to warm to room temperature. Separate the layers and extract the aqueous layer with 20% methanol in dichloromethane (10 mL×3). Dry combined organic layers (Na2SO4), filter and concentrate in vacuo to give a yellow residue. Purify the residue by silica gel flash chromatography to give an off-white foam. Suspend the foam in ACN and add HCL (5M in water; 1 mL). Freeze the resulting solution and lyophilize to obtain the title compound (50.5 mg, 0.12 mmol): mass spectrum (m/z): 446 (M+1-HCl).

Provenance & Evidence