4-Chlorobenzylamine → HCID 178429625, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxylate (1.27 g, 4.77 mmol) was dissolved in 4-chlorobenzylamine (11.6 mL, 95.4 mmol) and heated to 80° C. for 18 hours. After cooling to room temperature, the mixture was treated with 1 N HCl (100 mL). After chilling in the refrigerator for 2 hrs, the resulting thick precipitate was collected and washed with copious amounts of 1 N HCl until all unreacted 4-chlorobenzylamine had been washed away. The resulting off-white solid was dried in vacuo to give the title compound (1.60 g). 1H NMR (DMSO-d6) δ 2.27 (3 H), 4.53 (2 H), 4.72 (2 H), 5.06 (1 H), 7.38 (4 H), 8.52 (1 H), 10.49 (1 H), 12.95 (1 H). HPLC retention time: 2.73 minutes; MS (ESI−) for C17H15ClN2O3S m/z 361, 363.

Provenance & Evidence