Hydrochloric Acid → HCID 58838563, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,3-dimethyl-1-[(1R)-3-(methylamino)-1-phenylpropyl]-1,3-dihydro-2H-indol-2-one (Example 9, Step 2, 150 mg, 0.486 mmol) in dry tetrahydrofuran (3 mL) under nitrogen was added dropwise a solution of borane (1.0 M in tetrahydrofuran, 1.0 mL, 1.0 mmol, 2 equiv.) via a syringe. The resulting solution was heated at 70° C. with stirring for 2 h. Upon cooling, the reaction mixture was treated dropwise with a 2N aqueous solution of hydrochloric acid (2 mL), and was again heated at 60° C. for 20 minutes Upon cooling, solvent was removed under reduced pressure. To the residue was slowly added aqueous potassium carbonate (5 mL), and the mixture was extracted with dichloromethane (20 mL). The organic layer was washed with brine, dried (anhydrous sodium sulfate), and concentrated. Purification by Isco CombiFlash Companion chromatography (RediSep 4-g silica column, 0-15% methanol/dichloromethane/0.5% triethylamine) gave 100 mg (70%) of (3R)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine as a viscous brown liquid, which was dissolved dichloromethane (3 mL) and treated with an ethereal solution of hydrochloric acid (1 M, 0.37 mL, 0.37 mmol). To the resulting solution was added hexane until white powder formed, which was collected, washed with hexane, and dried in vacuo to yield (3R)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine hydrochloride as a yellow powder. MS (ES) m/z 295.3 ([M+H]+); HRMS: calculated for C20H26N2+H+, 295.2169; found (ESI, [M+H]+), 295.2160.

Provenance & Evidence