2-(2-METHOXY-ETHYL)-PIPERIDINE HYDROCHLORIDE synthesis

Yield: 10%

Reaction Conditions:

with hydrogenchloride;hydrogen;platinum(IV) oxide in ethanol under 3345.86 Torr; for 15 h;Parr shaker;

Steps:

15
Preparation 15 Preparation of 2-(2-methoxyethyl)piperidine hydrochloride salt.To a solution of 2-(2-methoxyethyl)pyridine (25 g, 182 mmol) in absolute ethanol (120 mL) was carefully added concentrated hydrochloric acid (5 mL) followed by platinum oxide (1.1 g, 4.8 mmol). The mixture was shaken for 15 h in a Parr shaker pressurized with hydrogen gas to 50 psig. The reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in water and extracted sequentially with dichloromethane and ethyl acetate. The extracts were combined and concentrated under reduced pressure to give unreacted starting material. The aqueous solution was concentrated under reduced pressure to afford the hydrochloride salt product as a white solid (3.14g, 10%). The product was used in a subsequent reaction without further purification. ¹H NMR (400 MHz, D₂O): δ 1.25-1.55 (m, 3H), 1.65-1.90 (m, 5H), 2.75-2.83 (m, 1 H), 3.05-3.15 (m, 1 H), 3.14- 3.23 (m, 4H), 3.41-3.50 (m, 2H).

References:

PFIZER INC.;CAMERON, Kimberly O'Keefe;PERRY, David Austen WO2010/67233, 2010, A1 Location in patent:Page/Page column 60