Butanal → 5-Butylidene-3-[5-(imidazo[1,2-a]pyridin-5-yl)pentyl]oxazolidine-2,4-dione
Reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][O:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:22](=O)[CH2:23][CH2:24][CH3:25].N1CCCCC1>C(O)C>[CH:22](=[C:18]1[O:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]2[N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=[CH:7][CH:8]=2)[C:19]1=[O:20])[CH2:23][CH2:24][CH3:25]Participants
5
Procedure
To a solution of 3.45 g (12 mmol) of 3-[5-(imidazo[1,2-a]pyridin-5-yl)pentyl]oxazolidine-2,4-dione and 1.08 ml (12 mmol) of n-butyraldehyde in 50 ml of ethanol, 0.12 ml (1.2 mmol) of piperidine was added, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/2→ethyl acetate/ethanol=10/1) to yield 1.36 g (33.2%, light yellow oily substance) of the desired product.
Workup
- temperatureby refluxing for 16 hours
- temperatureAfter the reaction mixture was cooled
- distillationthe solvent was distilled off
- dissolutionThe residue was dissolved in chloroform
- washwashed with saturated aqueous sodium hydrogen carbonate
- customdried
- distillationafter which the solvent was distilled off
- customThe residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/2→ethyl acetate/ethanol=10/1)
Sources & evidence
- ORD record
- ord-3678dcb115014c6cab1837f53c34c43c
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840732
Reaction notes
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