Methanol → 1-Dimethylamino-4-{methyl-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-piperidine-4-carboxylic acid methyl ester
Reaction equation
[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]Participants
Procedure
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).
Workup
- waitat 65° C. for 3 hours
- additionpoured on ice
- extractionThe mixture is extracted three times with ethyl acetate
- washwashed with brine
- dry with materialdried over sodium sulfate
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-b4f3445ab62a40ee9244800637ee6eaf
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703165B2
Reaction notes
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