HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 4-(5-Fluoroindol-3-yl)butyl methanesulfonate | HCID 11108889 | — |
| Reactant | 4-(5-Fluoro-1H-indol-3-yl)butanoic acid | HCID 15047268 | — |
| Reactant | 4-(5-fluoro-1H-indol-3-yl)butan-1-ol | HCID 18330271 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | 4-(2-oxo-2H-1-benzopyran-6-yl)piperazine, hydrochloride | HCID 131722709 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride | HCID 11178558 | — |
Reaction Steps
A mixture of 5.10 g (0.017 mol) of 4-(5-fluoroindol-3-yl)butyl methanesulfonate [obtainable by reaction of 4-(5-fluoroindol-3-yl)butanol (obtainable by lithium aluminium hydride reduction of 4-(5-fluoroindol-3-yl)butanoic acid, which can be prepared analogously to a Japp-Klingemann reaction, in THF) with methanesulfonyl chloride], 4.0 g (0.015 mol) of 4-(2-oxo-2H-1-benzopyran-6-yl)piperazine, hydrochloride (obtainable as described in Example 1), 200 ml of acetonitrile and 10.0 ml of triethylamine is reacted for 30 hours on a steam bath with stirring. After customary working up, 3-{4-[4-(2-oxo-2H-1-benzopyran-6-yl)-1-piperazinyl]butyl}-5-fluoroindole, hydrochloride, m.p. 293-295°, is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06251908B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-a1ba928dcce741318c149cd8af38cedd |
| Source note | uspto-grants-2001_06 |