HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → 5-methoxy-3-[N-(4-(4-fluoro-phenyl)-4-oxo-butyl)piperidin-3-ylmethyl]-1-H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane | HCID 2723778 | — |
| Reactant | 5-methoxy-3-(piperidin-3-ylmethyl)-1H-indole | HCID 18940825 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-methoxy-3-[N-(4-(4-fluoro-phenyl)-4-oxo-butyl)piperidin-3-ylmethyl]-1-H-indole | HCID 18940872 | — |
Reaction Steps
A mixture of compound of Description 6 [5-methoxy-3-(piperidin-3-ylmethyl)-1H-indole] (2 g; 0.0082 mol), sodium bicarbonate (0.68 g; 0.0082 mol), KI (0.087 g; 0.00053 mol) and 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [2.2 g (1,8 ml); 0.009 mol] in dry dimethylformamide (25 ml) and tetrahydrofuran (25 ml), was heated under reflux for 5 hours. After evaporation under vacuum, the residue was flash chromatographed on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0.5) and the desired compound was obtained. A solution of the compound in ethanol was saturated with gaseous hydrogen chloride, a solid was precipitated. The title compound hydrochloride was collected by filtration.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05834493 |
| Source dataset | uspto-grants-1998_11 |
| ORD ID | ord-8d8eec3188d9472e9532490aecf20030 |
| Source note | uspto-grants-1998_11 |