Hydrochloric Acid → 5-(4-bromo-2-formyl-N-propylanilino)pentanoic acid
Reaction equation
[CH2:1]([N:4]1C[CH2:8][CH2:7][CH2:6][C:5]1=O)[CH2:2][CH3:3].[OH-].[Na+].Cl.[C:14](=[O:17])([O-])[O-:15].[Na+].[Na+].[Br:20][C:21]1[CH:22]=[CH:23][C:24](F)=[C:25]([CH:28]=1)[CH:26]=[O:27]>O.CS(C)=O>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([N:4]([CH2:5][CH2:6][CH2:7][CH2:8][C:14]([OH:15])=[O:17])[CH2:1][CH2:2][CH3:3])=[C:25]([CH:26]=[O:27])[CH:28]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 1-propyl-2-piperidone (7.5 g) and 4N sodium hydroxide (26.6 ml) was refluxed for 4 hours. The mixture was cooled to 0° C. and conc. hydrochloric acid (8.85 ml) was added thereto. To the mixture were added sodium carbonate (11.3 g), 5-bromo-2-fluorobenzaldehyde (5.4 g) and DMSO (70 ml), and the resulting mixture was heated at 135° C. for 6 hours. The mixture was allowed to cool. Water was added and the mixture was extracted with THF-ethyl acetate. The organic layer was washed with water and saturated saline, and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography to obtain brown oil of 5-(4-bromo-2-formyl-N-propylanilino)pentanoic acid (8.8 g)
Workup
- temperaturewas refluxed for 4 hours
- temperaturethe resulting mixture was heated at 135° C. for 6 hours
- temperatureto cool
- extractionthe mixture was extracted with THF-ethyl acetate
- washThe organic layer was washed with water and saturated saline
- dry with materialdried over magnesium sulfate
- distillationAfter distilling off the solvent under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-d44a02121dd148fbbedc36122935c828
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362058B2
Reaction notes
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