Dichloromethane → C-(3-benzyloxyphenyl)-C-(3-chloropyrazin-2-yl)methylamine hydrochloride

Participants

Reaction Steps

2-[(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-isoindole-1,3-dione (2.76 g, 6.05 mmol) was dissolved in EtOH (12 mL) and CH2Cl2 (4 mL) charged with N2H4 (0.57 mL, 18.16 mmol) and allowed to react for 16 h at rt. The white precipitate was filtered and washed with EtOAc. The filtrate and organic washings were concentrated in vacuo, and purified via HPFC using a 100 g Jones silica gel column (50% EtOAc: Hex to 5% MeOH: CH2Cl2) to yield the desired product as a reddish oil; 1H NMR (CDCl3, 400 MHz) δ 5.04 (s, 2H), 5.52 (s, 1H), 6.85-6.98 (m, 2H), 7.21-7.26 (m, 2H), 7.30-7.41 (m, 5H), 8.26 (d, 1H, J=2.5 Hz), 8.52 (d, 1H, J=2.5 Hz); MS (ES) 326.25 (M+1), 328.23 (M+3), 329.24 (M+4).

Provenance & Evidence