Ethyl Acrylate → Ethyl 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propionate
Reaction equation
Cl.[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=[CH:10][C:3]1=2.[OH-].[Na+].[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21]>>[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([N:11]3[CH2:16][CH2:15][N:14]([CH2:21][CH2:20][C:19]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:12]3)=[CH:8][CH:9]=[CH:10][C:3]1=2Participants
Procedure
5.05 g (19.8 mmol) of 1-benzo[b]thiophen-4-yl-piperazine hydrochloride was added to an aqueous solution of sodium hydroxide, and the mixture was extracted with dichloromethane. The extraction solution was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in 50 ml of ethanol and ethyl acrylate (2.44 ml, 21.8 mmol) was added thereto, and then the reaction mixture was refluxed with heating for 4 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. Diisopropyl ether was added to the residue and insoluble matter precipitated was obtained by filtration, washed with diisopropyl ether, and dried to obtain ethyl 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propionate (5.26 g) as white powder.
Workup
- extractionthe mixture was extracted with dichloromethane
- dry with materialThe extraction solution was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- dissolutionThe obtained residue was dissolved in 50 ml of ethanol
- temperaturethe reaction mixture was refluxed
- temperaturewith heating for 4 hours
- concentrationconcentrated under reduced pressure
- additionDiisopropyl ether was added to the residue and insoluble matter
- customprecipitated
- customwas obtained by filtration
- washwashed with diisopropyl ether
- customdried
Sources & evidence
- ORD record
- ord-619628404ffc4b198c2b0dfa7247eec0
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071600B2
Reaction notes
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