1,2,3,4-Tetrahydro-1-naphthylamine → HCID 11551484, compound

Participants

Reaction Steps

A solution of 1,2,3,4-tetrahydronaphthalen-1-amine (0.82 mL, 5.73 mmol), 2,4-difluoro-1-(methylsulfonyl)benzene (1.1 g, 5.73 mmol) and diisopropylethylamine (2.0 mL, 11.46 mmol) in CH3CN (15 mL) was stirred at 60° C. for 48 h. The solvent was concentrated in vacuo, the residue was taken up in dichloromethane and washed with water and brine, dried, and concentrated under reduced pressure to yield 2.1 g of a yellow oil. The residue was purified by PTLC (20% ethyl acetate in hexanes) to give 720 mg (39%) of the desired aniline: 1H NMR (400 MHz, CDCl3) δ 7.78 (dd, 1H), 7.28-7.13 (m, 3H), 6.60 (dd, 1H), 6.51-6.45 (m, 2H), 4.62 (dd, 1H), 2.96 (s, 3H), 2.91-2.74 (m, 2H), 2.05-1.98 (m, 2H), 1.91-1.85 (m, 2H). MS (ESI) m/z: Calculated: 319.39; Observed: 661.0 (2M++23).

Provenance & Evidence