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 methylene chloride. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in 50 ml of ethanol and ethyl acrylate (2.44 ml, 21.8 mmol) was added thereto, then the reaction mixture was refluxed for 4 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Isopropyl ether was added to the residue to filter out insoluble matters. The insoluble matters were washed with isopropyl 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 methylene chloride
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in 50 ml of ethanol
- temperaturethe reaction mixture was refluxed for 4 hours
- concentrationconcentrated under reduced pressure
- additionIsopropyl ether was added to the residue
- filtrationto filter out insoluble matters
- washThe insoluble matters were washed with isopropyl ether
- customdried
Sources & evidence
- ORD record
- ord-1077e94f2ff949fdb2e434fb34f8ce94
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618109B2
Reaction notes
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