Sodium Hydroxide → 1-Benzylpiperidine-3-carboxylic acid

Participants

Reaction Steps

To a solution 3.0 g (9.7 mmol) of 1-benzylpiperidine-3-carboxylic acid benzyl ester (Example A21) in methanol (20 mL) was added 1N sodium hydroxide (20 mL), and the reaction is stirred at room temperature for 18 hours. The methanol is removed in vacuo and the basic aqueous solution is acidified to pH 4 with 1.0 M hydrochloric acid. After washing with ethyl acetate, the aqueous acid layer is lyophilized. The solid is suspended in methanol (10 mL), stirred for 10 minutes and filtered. The filtrate is evaporated in vacuo to afford the title compound (2.0 g). 1H NMR (200 MHz, DMSO-d6): δ 7.38-7.23 (m, 5H), 3.58 (s, 2H), 2.98-2.40 (m, 3H), 2.30-1.25 (m, 6H).

Provenance & Evidence