Water → 1-{4-[(3-Fluorobenzyl)oxy]phenyl}methanamine

Participants

Reaction Steps

(Aldrich data.) To a LiAlH4 (5.02 g, 132.0 mmol) suspension in THF (400 mL) was added dropwise a THF (30 mL) solution of 4-(3-fluorobenzyloxy)benzonitrile (10.00 g, 44.0 mmol) at 0° C. The mixture was stirred at room temperature (16 h) and H2O (4 mL) was added dropwise at 0° C. followed by an aqueous NaOH solution (2 mL, 15% w/w), and then H2O (4 mL). The mixture was stirred at room temperature (2 h), and the precipitate filtered through a Celite® pad and the pad washed with CH2Cl2. The filtrate was concentrated in vacuo to obtain a white solid (8.82 g, 86%): Rf=0.00 (hexanes/EtOAc 9/1); 1H NMR (CDCl3) δ 1.61 (br s, NH2), 3.79 (s, CH2NH2), 5.04 (s, CH2O), 6.90-7.04 (m, 3 ArH) 7.13-7.37 (m, 5 ArH); HRMS (M-NH2+) (ESI+) 215.088 [M-NH2+] (calcd for C14H12O+ 215.087).

Provenance & Evidence