Ethanol → HCID 15860308, compound

Participants

Reaction Steps

(trans)-2-(2-Fluoro-5-methoxyphenyl)cyclopropanemethanamine: A suspension of (trans)-2-(2-fluoro-5-methoxyphenyl)cyclopropane carbonitrile (5.0 g, 26 mmol), PtO2 (200 mg), and CHCl3 (10 mL) in EtOH (65 mL) was hydrogenated in a Parr apparatus at 55 psi for 3 h. The catalyst was filtered through a plug of celite and the solvents were removed. The resulting hydrochloride salt was then partitioned between CH2Cl2 and 10% K2CO3. The organic layer was separated, dried over K2CO3, and concentrated to afford the title compound as the free amine, 3.8 g (74%): 1H NMR (250 MHz, CDCl3) δ0.79-0.82 (m, 1H), 0.90-0.95 (m, 1H), 1.49 (br s, 2H), 1.70-1.76 (m, 1H), 1.82-1.86 (m, 1H), 2.60-2.74 (m, 2H), 3.75 (s, 3H), 6.35-6.42 (m, 1H), 6.50-6.62 (m, 1H), 6.85-6.90 (m, 1H).

Provenance & Evidence