1-CBZ-4-(3-AMINOPHENOXY)-PIPERIDINE synthesis

Yield:872037-69-9 54%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane at 22; for 1 h;

Steps:

17

4-(3-tert-Butoxycarbonylamino-phenoxy)-piperidine-1-carboxylic acid benzyl ester (11.8 g, 27.6 mmol) is dissolved in a solution of trifluoroacetic acid in dichloromethane (25% v/v, 20 mL). The reaction mixture is stirred at 22°C for 60 min. After removal of the solvent, the oily residue is dissolved in dichloromethane (250 mL) and neutralized with 0.2 N aqueous sodium hydroxide solution (250 mL) and extracted with dichloromethane (10 x 100 mL) followed by ethyl acetate (5 x 100 mL). The combined organic phases are dried over anhydrous sodium sulfate. After removal of solvent, the crude product is purified on silica gel chromatography with dichloromethane-methanol to give a light brown oil (4.84 g, 54 %, ES+(m/z) 327.3 [M+H]).

References:

EP1609789,2005,A1 Location in patent:Page/Page column 15