Sodium Hydroxide → 2-[4-(2-Fluorophenyl)piperazin-1-yl]ethanamine

Participants

Reaction Steps

1-(Cyanomethyl)-4-(2-fluorophenyl)piperazine (9.0 g, 41.0 mmol) was added in portions to a suspension of LiAlH4 (2.34 g, 61.6 mmol) in diethyl ether (200 ml) over 1/2 hour. The mixture was heated to reflux for 5 hours. Water (3 ml) was slowly added to the mixture, followed by a 15% solution of sodium hydroxide in water (3 ml) and water (9 ml). The inorganic solids were removed by filtration, and the filtrate was dried over MgSO4. The solvent was removed in vacuo to give the product (16.76 g, 70% yield) as an amber oil which slowly crystallized to a colorless solid, mp 108°-112° C. IR (KBr) 1502 cm-1 ; mass spectrum m/z 224 (MH+); 1H NMR (CDCl3) δ1.38 (s, 2H, NH2), 2.33-3.23 (m, 12H, NCH2), 6.80-7.06 (m, 4 H, Ph-H).

Provenance & Evidence