Dichloromethane → HCID 55088291, compound

Participants

Reaction Steps

To a suspension of LAH (1.25 g, 27 mmol) in dry diethyl ether (100 mL) was added dropwise a solution of 2-benzyloxy-N-(4-fluoro-phenyl)-acetamide (33) (6.9 g, 27 mmol) in dry diethyl ether (100 mL). The addition was such as a reflux was maintained. Once the addition was completed, the reaction mixture was heated to reflux for 4 h, then poured into ice-water and DCM was added. In order to break down the aluminium salt, 2M aqueous sodium hydroxide solution was added until strong basic pH was obtained. The layers were separated and the aqueous layer was washed with DCM, dried and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (5-50% B, 100 g, 12 CV, 60 mL/min) to afford 5.5 g (84%) of (2-benzyloxy-ethyl)-(4-fluoro-phenyl)-amine (34) as a yellow oil. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 44.0, 68.3, 72.8, 113.7 (d, JCF=7 Hz), 115.3 (d, JCF=22 Hz), 127.5, 127.6 (d, JCF=3 Hz), 128.3, 137.8, 144.5, 154.1, and 157.2.

Provenance & Evidence