Potassium Iodide → 5-(2-Hydroxyethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
Reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.Br[CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[OH:13][CH2:12][CH2:11][N:6]1[CH2:7][CH2:8][C:9]2[S:1][CH:2]=[CH:3][C:4]=2[CH2:5]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (0.86 g), 2-bromoethanol (0.66 g), potassium carbonate (2.58 g) and potassium iodide (3.10 g) in N,N-dimethylformamide (20 ml) was stirred at 70° C. for 2 hours. After cooling, ethyl acetate and water were added thereto. The organic layer was separated, washed with water twice, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of methanol and dichloromethane (1:10) as an eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure to give 5-(2-hydroxyethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (0.53 g) as an oil.
Workup
- temperatureAfter cooling
- customThe organic layer was separated
- washwashed with water twice
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel using a mixed solvent of methanol and dichloromethane (1:10) as an eluent
- additionThe fractions containing the objective compound
- customwere collected
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-35b7f4d2a7a245cca166b1464290e52b
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166598B2
Reaction notes
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