N-Acetyl-4-piperidone → HCID 66743355, compound
Reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:23][C:24]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[S:26][C:25]=1[C:35]([NH2:37])=[O:36]>C(O)(=O)C>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([NH:23][C:24]3[CH:28]=[C:27]([C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[S:26][C:25]=3[C:35](=[O:36])[NH:37]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Participants
5
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 1-acetyl-4-piperidone (0.130 g, 0.920 mmol) and p-toluenesulfonic acid monohydrate (0.004 g, 0.02 mmol) in acetic acid (4 mL) was added 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.050 g, 0.23 mmol). The mixture was heated at 80° C. for 5 h. Then, the reaction was allowed to cool to room temperature and concentrated. The obtained residue was dissolved in methanol (25 mL) and the solution was stirred with solid NaHCO3 (1.5 g) for 20 min. Then, the solution was filtered, and the filtrate was concentrated. The obtained residue was triturated with H2O. The obtained yellow solid was triturated with hot ethyl acetate to give the title compound (0.0407 g, 52%) as a yellow solid:
Workup
- temperatureto cool to room temperature
- concentrationconcentrated
- dissolutionThe obtained residue was dissolved in methanol (25 mL)
- filtrationThen, the solution was filtered
- concentrationthe filtrate was concentrated
- customThe obtained residue was triturated with H2O
- customThe obtained yellow solid was triturated with hot ethyl acetate
Sources & evidence
- ORD record
- ord-3827b56836204ff1a62538c105404d56
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691828B2
Reaction notes
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