Methanol → 1-Dimethylamino-4-{methyl-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-piperidine-4-carboxylic acid methyl ester

Reaktionsgleichung

[C:1]([C:3]1([N:12]([CH3:25])[C:13](=[O:24])[CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[CH2:8][CH2:7][N:6]([N:9]([CH3:11])[CH3:10])[CH2:5][CH2:4]1)#N.S(=O)(=O)(O)[OH:27].[CH3:31][OH:32]>>[CH3:31][O:32][C:1]([C:3]1([N:12]([CH3:25])[C:13](=[O:24])[CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[CH2:8][CH2:7][N:6]([N:9]([CH3:11])[CH3:10])[CH2:5][CH2:4]1)=[O:27]

Komponenten

Edukt 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 67226420N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-N-methyl-2-(2,4,6-trimethylphenyl)-acetamide

Produkt 1

HCID 672257031-Dimethylamino-4-{methyl-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-piperidine-4-carboxylic acid methyl ester

Versuchsvorschrift

1.30 g N-(4-Cyano-1-dimethylamino-piperidin-4-yl)-N-methyl-2-(2,4,6-trimethyl-phenyl)-acetamide (from Step 2) is dissolved in 2.6 ml methanol, and 1 ml concentrated sulfuric acid is added. The mixture is stirred at room temperature for 3 hours, then at 65° C. for 3 hours, then poured on ice. The mixture is extracted three times with ethyl acetate, washed with brine, dried over sodium sulfate, and the solvent evaporated. Thus, 750 mg 1-Dimethylamino-4-{methyl-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-piperidine-4-carboxylic acid methyl ester is obtained. 1H-NMR (CDCl3): 6.80 ppm (s, 2H), 3.60 ppm (s, 5H), 3.15 ppm (s, 3H), 3.15 ppm (s, 3H), 2.85 ppm (m, broad, 4H), 2.45 ppm (s, 6H), 2.30 ppm (m, broad, 2H), 2.20 (s, 3H), 2.15 (s, 6H), 2.10 ppm (m, broad, 2H).