Sodium borohydride → 3-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-ol

Participants

Reaction Steps

A mixture of ethyl 3-(4-(methoxyphenyl)piperazin-1-yl)propanoate (17a) (0.0048 mol) and sodium borohydride (5.4 g, 0.14 mol) in 100 mL anhydrous ethanol was refluxed for overnight (12 h). The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was concentrated on rotavapor. The residue was diluted with DCM, washed with saturated aqueous NaHCO3 solution (25 mL×2) and water (25 mL), dried over sodium sulphate (Na2SO4) and evaporated under reduced pressure to give 3-(4-(methoxyphenyl)piperazin-1-yl)propan-1-ol (21a) which was purified by silica gel column chromatography using 0-5% gradient of ethyl acetate and methanol. White solid, 0.6 g (50%). 1H NMR (400 MHz, CDCl3): δ 1.75 (quintet, J=5.2 Hz, 2H); 2.69 (t, J=6.0 Hz, 2H), 2.74 (broad s, 4H); 3.08 (broad s, 4H); 3.82 (t, J=5.2 Hz, 2H); 3.85 (s, 3H); 5.35 (broad s, 1H); 6.84-6.86 (m, 1H); 6.90-6.93 (m, 2H); 6.97-7.02 (m, 1H). MS (ESI): m/z=251.40 (M+H+).

Provenance & Evidence