Hydrochloric Acid → HCID 58651192, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, to a solution of (2R)-2-Amino-1-[4-(2-methoxy-phenyl)-piperazin-1-yl]-3-pyridin-2-yl-propan-1-one (1.02 g; 3 mmol, from Example 12) in THF (10 mL) was added, dropwise, BF3.Et2O (0.37 mL; 3 mmol). The reaction mixture was heated to reflux, BH3.THF (1.0M/THF) (4.3 mL; 4.3 mmol) was added dropwise at reflux, and the mixture stirred at reflux for 2.5 hours. The mixture was cooled to 0–5° C., cautiously treated with 3N HCl (10 mL), stirred at ambient temperature for 1 hour. The mixture was heated to reflux for 5 minutes, cooled to ambient temperature, concentrated on a rotary evaporator to remove THF. The aqueous residue was washed with ether (5 mL), and the ether layer discarded. The aqueous layer was rendered basic (pH 9–10) with 2.5N NaOH, and the product extracted into ethyl acetate (25 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and the solvent removed in vacuo to yield the free base of the title compound as an amber oil (804 mg; 82%), MS EI, M+ @ m/z 326; 1H NMR, 400 MHz, DMSO-d6.

Provenance & Evidence