Ammonium formate → HCID 58860672, compound

Participants

Reaction Steps

Dissolve (S)-1,4-dibenzyl-2-(2-naphthalen-1-yl-ethyl)-piperazine (3.33 g, 7.92 mmol) in ethanol (100 mL). Add ammonium formate (2.99 g, 47.5 mmol) and palladium (666 mg, 5 wt. % on carbon) and heat to reflux. After 6 h 30 min, filter the palladium on carbon and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (2.5%–10%) and 7N ammonia in methanol-methylene chloride (20%) as the eluent to give 716 mg (38%) of (S)-2-(2-naphthalen-1-yl-ethyl)-piperazine, 1.1 g of (S)-1-benzyl-3-(2-naphthalen-1-yl-ethyl)-piperazine, and 290 mg of (S)-1-benzyl-2-(2-naphthalen-1-yl-ethyl)-piperazine.

Provenance & Evidence