2-Mercaptoethanol → N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-(2-hydroxyethylthio)acetamide
Reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[OH-].[K+].[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:28])[CH2:26]Cl)[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CO>[N:7]1([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:28])[CH2:26][S:1][CH2:2][CH2:3][OH:4])[CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
0.12 ml of 2-mercaptoethanol was added to a solution of 0.13 g of 85% potassium hydroxide and 0.50 g of N-[3-(4-piperidinomethyl-2-pyridyloxy)propyl]-2-chloroacetamide [prepared as described in step (a) above] in 10 ml methanol, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, the concentrate was mixed with water, and the resulting aqueous mixture was extracted with chloroform. The extract was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of ethanol and chloroform as the eluent, to give 0.43 g (yield 77%) of the title compound as an oil.
Workup
- concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
- additionthe concentrate was mixed with water
- extractionthe resulting aqueous mixture was extracted with chloroform
- concentrationThe extract was concentrated by evaporation under reduced pressure
- customthe residue was purified by column chromatography through silica gel
- additionby volume mixture of ethanol and chloroform as the eluent
Sources & evidence
- ORD record
- ord-19df28b2737b4a69a239e6d9146cc7db
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616579
Reaction notes
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