Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-tert-Butoxycarbonyl-4-[(4-hydroxyphenyl)sulfanyl]piperidine | HCID 18538757 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18539185 | HCID 18539185 | 95.2% |
Reaction Steps
A mixture of 1-tert-Butoxycarbonyl-4-[(4-hydroxyphenyl)sulfanyl]piperidine (3.09 g, 10.0 mmol), ethyl iodide (1.04 mL, 13.0 mmol), and potassium carbonate (1.80 g, 13.0 mmol) in DMF (15 mL) was stirred at 60° C. for 20 hours. The reaction mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate (40 mL), washed with water (10 mL), 0.5 N sodium hydroxide solution (10 mL×3), brine (10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using ethyl acetate/hexane (1/19 to 1/9) as eluent to afford the title compound (3.21 g, 9.52 mmol, 95%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06562978B1 |
|---|
| Source dataset | uspto-grants-2003_05 |
|---|
| ORD ID | ord-9ae525ab10d842c0b02a0b8390a13d2c |
|---|
| Source note | uspto-grants-2003_05 |
|---|