Diethyl Ether → HCID 59536270, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(3-fluorophenethyl)-4-(trifluoromethyl)benzamide (2.8 g, 8.9 mmol) and phosphoric pentoxide (0.6 g, 0.45 mmol) in polyphosphoric acid (62.0 g, 8.9 mmol) was heated at 170° C. for 75 min. The hot reaction mixture was poured into ice and KOH (20% W/V, 50 mL) was added followed by diethyl ether (100 mL) and stirred for 5 mins. Additional KOH was added until pH˜11.0 was achieved. Then, EtOAc (200 mL) was added and the mixture continued stirring at RT for an additional 5 min. and the ethyl acetate layer was separated. The aqueous layer was back-extracted with ethyl acetate (3×200 mL). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, and concentrated under vacuum to provide 6-fluoro-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline as a yellow oil. MS (ESI pos. ion) m/z: 294 (M+H).

Provenance & Evidence