Acetic Acid → HCID 14553815, compound

Reaction equation

[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH:15]([CH3:26])[CH2:16][N:17]2[CH2:22][CH2:21][CH:20]=[C:19]([CH2:23][O:24][CH3:25])[CH2:18]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>C(O)C.[C].[Pd]>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH:15]([CH3:26])[CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH:19]([CH2:23][O:24][CH3:25])[CH2:18]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

N-[3-(m-Phenoxyphenyl)-2-methylpropyl]-3-methoxymethyl-1,2,5,6-tetrahydropyridine (0.2 g) was dissolved in ethanol (20 ml), followed by addition of acetic acid (1 ml) thereto. To the resultant mixture, 5% palladium-carbon (0.2 g) was added at room temperature under nitrogen stream, and then hydrogenation was carried out under nitrogen stream. After absorption of hydrogen was completed, the catalyst was removed by filtration, and the filtrate was combined with 15% aqueous sodium hydroxide solution (20 ml) and extracted with diethyl ether. The ether extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to give N-[3-(m-phenoxyphenyl)-2-methylpropyl]-3-methoxymethylpiperidine (0.19 g).