Hydrogen Bromide → HCID 20069068, compound

Participants

Reaction Steps

A suspension of 294 mg (0.9 mmol) of 1-aminomethyl-3-cyclohexyl-3,4-dihydro-5-methoxy-8-methyl-1H-2-benzopyran hydrochloride, from Step 3, in 8 mL of glacial acetic acid and 8 mL of 48% aqueous hydrobromic acid was stirred at reflux temperature for 2 h. The reaction mixture was concentrated in vacuo to remove most of the hydrobromic acid. The aqueous concentrate was adjusted to pH 8.0 with 50% aqueous sodium hydroxide solution and saturated aqueous sodium bicarbonate solution. The resultant aqueous solution was extracted with 2×100 mL of methylene chloride and the combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel eluted with 5% methanol in methylene chloride to give the free amine. The amine was treated with diethyl ether saturated with anhydrous hydrogen chloride and the resultant precipitate was crystallized from methanol/ether to afford 152 mg (55% yield) of the title compound, m.p.>280° C.(dec); MS DCI-NH3M/Z: 276 (M+H)+. Analysis calculated for C17H26CINO2 +0.2H2O: C, 64.73; H, 8.42; N, 4.47. Found: C, 64.78; H, 8.33; N, 4.26.

Provenance & Evidence