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201609-38-3

4-METHOXY-4-PHENYLPIPERIDINE synthesis

3synthesis methods
1-Piperidinecarboxylic acid, 4-methoxy-4-phenyl-, 1,1-dimethylethyl ester

201609-37-2
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4-METHOXY-4-PHENYLPIPERIDINE

201609-38-3
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Yield:201609-38-3 49%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;water at 0 - 20; for 1.5 h;

Steps:

55 EXAMPLE 55 4-Methoxy-4-phenylpiperidine

1-t-Butoxycarbonyl-4-methoxy-4-phenylpiperidine (150 mg, 0.51 mmol) was dissolved in a mixed solvent of 1,4-dioxane (20 ml) and concentrated hydrochloric acid (10 ml). The resulting solution was stirred at 0° C. for a while and then gradually returned to a room temperature spending 1.5 hours. The reaction solution was neutralized by adding with sodium hydroxide aqueous solution (1 N), and then the solvent was evaporated under a reduced pressure. The thus obtained residue was mixed with ethyl acetate and water, the reaction product was extracted with ethyl acetate, washed with water and saturated brine and dried with anhydrous sodium sulfate. Then the solvent was evaporated under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 49 mg of the title compound (0.25 mmol, 49% in yield). 1H-NMR (CDCl3) δ 1.84-1.92 (2 H, m), 1.99-2.05 (2 H, m), 2.90-2.99 (5 H, m), 3.03-3.11 (2 H, m), 7.24-7.43 (5 H, m); MW 191.27 (C12H17NO); Mass spectrum EI m/z 191 (M)+

References:

US6355642,2002,B1 Location in patent:Page column 31

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