Ammonium formate → HCID 45115805, compound

Participants

Reaction Steps

Dissolve (S)-1,4-dibenzyl-2-(2-pyridin-3-yl-ethyl)-piperazine (1.6 g, 4.31 mmol) in ethanol (30 mL). Add ammonium formate (1.63 g, 25.8 mmol) and palladium (240 mg, 5 wt. % on carbon) and heat to reflux. After 3 hours 30 minutes, add additional ammonium formate (1.63 g, 25.8 mmol). After 3 hours, filter the palladium on carbon and concentrate the filtrate. Slurry the residue in water and methylene chloride, basify with 5N NaOH, and extract with methylene chloride and chloroform-isopropanol (3:1 mixture). Dry the extracts over sodium sulfate, filter and concentrate the filtrate. Purify by silica gel chromatography using 7N ammonia in methanol-methylene chloride (2.5%–15%) as the eluent to give (261 mg, 32%) of the title compound: mp 104–110° C.; mass spectrum (ion spray): m/z=192 (M+1). 1H NMR (DMSO-d6, D2O): δ8.42 (d, 1H), 8.38 (dd, 1H), 7.63 (dt, 1H), 7.31 (dd, 1H), 2.38–2.83 (m, 8H), 2.18 (dd, 1H), 1.50 (dd, 2H).

Provenance & Evidence