Hydrochloric Acid → N-{1-[4-(3,4-dichlorobenzoyl)-piperidin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH:21]([NH:25][C:26](=[O:34])[C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)[CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]3)OCC[O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[C:9]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH:21]([NH:25][C:26](=[O:34])[C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)[CH:22]([CH3:23])[CH3:24])[CH2:16][CH2:15]1)=[O:10]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide (0.4 g, 0.791 mmol), aqueous HCl (10 mL, 6 N), and acetonitrile (10 mL) was refluxed for 2 h. After concentrating the reaction mixture, the residue was stirred with ethyl acetate and water. Sodium hydroxide solution (6 N) was added until the aqueous layer was pH 8. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over magnesium sulfate and concentrated to give N-{1-[4-(3,4-dichlorobenzoyl)-piperidin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide which was converted to the hydrochloride salt by adding 2 molar excess ethereal HCl (1 M) to an ether solution of the free base.