HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(Bromomethyl)benzenesulfonyl chloride → 4-[4-(Bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(Bromomethyl)benzenesulfonyl chloride | HCID 2734409 | — |
| Reactant | 4-(2-Oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester | HCID 23447514 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 4-[4-(Bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone | HCID 23447610 | 49% |
Reaction Steps
To a solution of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (500 mg) in ethyl acetate (15 ml) and sodium bicarbonate solution (10 ml) was added at 0° C. 4-(bromomethyl)benzenesulfonyl chloride (453 mg), and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated, washed with brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane: ethyl acetate=2:3) to give colorless crystals of 4-[4-(bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (437 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06680312B2 |
| Source dataset | uspto-grants-2004_01 |
| ORD ID | ord-5e6e23d9dd0349eebda7318cbccd75b9 |
| Source note | uspto-grants-2004_01 |