Benzimidazole → HCID 59803191, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1H-benzo[d]imidazole (0.106 g, 0.90 mmol) and (R)—N-(3-bromo-4-chlorobenzyl)-1-phenylethanamine 75 (0.247 g, 0.76 mmol) was added potassium carbonate (0.141 g, 1.0 mmol), copper(I) iodide (0.023 g, 0.12 mmol), and NMP (0.8 mL). The reaction mixture was degassed and heated to 150° C. for 3 d, diluted with EtOAc, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 40% to 100% EtOAc in hexanes) gave (1R)—N-(3-(1H-benzo[d]imidazol-1-yl)-4-chlorobenzyl)-1-phenylethanamine 76 (0.053 g, 19% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.38 (d, J=6.7 Hz, 3H), 3.69 (s, 2H), 3.82 (q, J=6.7 Hz, 1H), 7.20-7.43 (m, 11H), 7.55 (d, J=8.2 Hz, 1H), 7.79 (d, J=7.2 Hz, 1H), 8.04 (s, 1H). Mass spectrum: calculated for C22H20ClN3 361.1. found 362.2 (M++1).

Provenance & Evidence