Aluminium lithium hydride → 4-(1,4-Dimethylpiperidin-4-yl)aniline

Participants

Reaction Steps

To a solution of ethyl 4-(4-aminophenyl)-4-methylpiperidine-1-carboxylate (444 mg, 1.692 mmol) in THF (10 mL) was added solid LAH (321 mg, 8.46 mmol) portion-wise. The formation of bubbles were observed during addition. The reaction mixture was stirred at room temperature for 20 min. The reaction mixture was diluted with methylene chloride and 15 mL of 1N NaOH was added slowly to destroy excess LAH. The resulting mixture was separated by separatory funnel. The organic layer was washed with water and concentrated. The residue was purified by MPLC (ISCO, 6% ammonia/MeOH/CH2Cl2, 40 g silica gel column) to give 267 mg colorless oil. (M+H)+=205.18.

Provenance & Evidence