Hydrochloric Acid → HCID 58651188, compound

Participants

Reaction Steps

To a solution of (2R)-2-Amino-1-[4-(2-methoxy-phenyl)-piperazin-1-yl]-3-pyridin-3-yl-propan-1-one (6.23 g; 18.3 mmol, from Example 2) in THF (60 mL) was added, dropwise, BH3.THF (1.0M/THF) (73 mL; 73 mmol). The mixture was stirred at reflux for 2.5 hours, then allowed to stir at ambient temperature overnight. The mixture was cooled to 0–5° C., cautiously treated with 5M HCl (30 mL), stirred at ambient temperature for 4 hours. The mixture was then concentrated on a rotary evaporator to remove THF, diluted with water (30 mL), and the pH adjusted to 10 with concentrated ammonium hydroxide. The product was extracted into ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and the solvent removed in vacuo to yield the title compound as a free base (5.24 g.; 88%). The analytical sample was converted to the hydrochloride salt with ethereal HCl to yield a white crystalline solid, m.p. 168–169° C.; MS (+) ESI, [M+H]+ @ m/z 327; 1H NMR, 400 MHz, DMSO-d6. Analysis for C19H26N4O.HCl.H2O.0.25 C2H6O Calculated: C, 62.21; H, 8.16; N, 14.88 Found: C, 61.72; H, 7.65; N, 14.17.

Provenance & Evidence