Ethyl Acetate → (1-Benzylpiperidin-4-yl)methanol

Participants

Reaction Steps

1.42 g (0.0375 mol) of lithium aluminium hydride were suspended in 20 ml of THF. 1.548 g (0.00623 mol) of ethyl 1-benzylpiperidine-4-carboxylate were slowly added dropwise at 0°. The mixture was heated to 70° and boiled at reflux for 16 hrs. The reaction mixture was treated with 70 ml of ethyl acetate, 6.5 ml of water and 1.5 ml of 2N aqueous NaOH. The mixture was stirred for 1 hr., the precipitate was filtered off and the filtrate was concentrated. The residue was chromatographed on silica gel with methanol/dichloromethane (1:9) as the eluent. 1.16 g (91%) of 1-benzyl-4-hydroxymethylpiperidine were obtained.

Provenance & Evidence