8-Aminoquinoline → 1-Acetyl-N-(quinolin-8-yl)-4-piperidinecarboxamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl.[C:13]([N:16]1[CH2:21][CH2:20][CH:19]([C:22](Cl)=[O:23])[CH2:18][CH2:17]1)(=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:13]([N:16]1[CH2:17][CH2:18][CH:19]([C:22]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)=[O:23])[CH2:20][CH2:21]1)(=[O:15])[CH3:14]Participants
Conditions
- Temperature
- 80 °C
Procedure
A solution of 8-aminoquinoline (48.50 g) in dimethylformamide (300 ml) was stirred at 80° C., under nitrogen, as a mixture of 1-acetylpiperidine-4-carbonyl chloride hydrochloride (106.30 g) and potassium carbonate (93.0 g) was added in portions. The slurry was stirred at 80° C. overnight, quenched with water (1200 ml) and extracted with dichloromethane. The extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was purified first by high performance liquid chromatography (silica; 25:1 dichloromethane-methanol), followed by flash chromatography (silica; 50:1 dichloromethane-methanol). The appropriate fractions were collected and evaporated to give 58.5 g (58.6%) of product, as an oil.
Workup
- additionwas added in portions
- customquenched with water (1200 ml)
- extractionextracted with dichloromethane
- dry with materialThe extracts were dried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate was evaporated
- customThe residue was purified first by high performance liquid chromatography (silica; 25:1 dichloromethane-methanol)
- customThe appropriate fractions were collected
- customevaporated
Sources & evidence
- ORD record
- ord-32b67ffd99d94f81a0c82546cf166794
- Source dataset
- uspto-grants-1996_03
- Patent number
- US05500423
Reaction notes
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